# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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. 
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data_exp_62me2bpdci
_database_code_depnum_ccdc_archive 'CCDC 1953894'
loop_
_audit_author_name
_audit_author_address
'Christopher Richardson'
;University of Wollongong
Australia
;
_audit_update_record             
;
2019-09-16 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-08-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
"dimethyl 2-iodo-[1,1'-biphenyl]-4,4'-dicarboxylate"
_chemical_formula_moiety         'C16 H13 I O4'
_chemical_formula_sum            'C16 H13 I O4'
_chemical_formula_weight         396.16
_chemical_melting_point          388.15
_chemical_oxdiff_formula         C16H13O4I
_chemical_oxdiff_usercomment     
'Iodo biphenyl dicarboxylate from DCM/Pet Spirit'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8767(4)
_cell_length_b                   10.0877(5)
_cell_length_c                   10.6978(5)
_cell_angle_alpha                105.230(4)
_cell_angle_beta                 107.161(4)
_cell_angle_gamma                102.068(4)
_cell_volume                     744.83(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10803
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      30.6590
_cell_measurement_theta_min      2.1690
_shelx_estimated_absorpt_T_max   0.863
_shelx_estimated_absorpt_T_min   0.478
_exptl_absorpt_coefficient_mu    2.162
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.15 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             388
_exptl_crystal_recrystallization_method 'CH2Cl2 / Pet. Spirit'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14566
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        29.000
_diffrn_reflns_theta_max         30.660
_diffrn_reflns_theta_min         2.125
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'HyPix Bantam HPC-3000'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  62.00   0.50    7.00    --   20.00  54.00 -30.00  128
  2  ω     43.00  69.00   0.50    7.00    --   20.00  54.00  30.00   52
  3  ω     69.00  95.00   0.50    7.00    --   20.00  54.00  60.00   52
  4  ω     51.00  98.00   0.50    7.00    --   20.00  54.00 116.28   94
  5  ω     14.00  40.00   0.50    7.00    --   20.00  54.00 116.28   52
  6  ω     78.00 104.00   0.50    7.00    --   20.00  54.00-150.00   52
  7  ω    -17.00  60.00   0.50    7.00    --   20.00  54.00-150.00  154
  8  ω    -20.00   6.00   0.50    7.00    --   20.00  54.00  30.00   52
  9  ω    -33.00 108.50   0.50    7.00    --   20.00  54.00 -60.00  283
 10  ω    -35.00  77.50   0.50    7.00    --   20.00  54.00   0.00  225
 11  ω    -65.00  71.50   0.50    7.00    --   20.00  54.00 -90.00  273
 12  ω    -69.00 -43.00   0.50    7.00    --   20.00  54.00   0.00   52
 13  ω    -73.00  52.50   0.50    7.00    --   20.00  54.00  60.00  251
 14  ω    -72.00 -19.00   0.50    7.00    --   20.00  54.00 150.00  106
 15  ω    -66.00 -40.00   0.50    7.00    --   20.00  54.00  90.00   52
 16  ω    -66.00 -23.00   0.50    7.00    --   20.00  54.00  30.00   86
 17  ω    -72.00 -26.00   0.50    7.00    --   20.00  54.00 -30.00   92
 18  ω    -64.00 -39.00   0.50    7.00    --   20.00  54.00-120.00   50
 19  ω    -72.00 -46.00   0.50    7.00    --   20.00  54.00-150.00   52
 20  ω    -65.00  -8.00   0.50    7.00    --   20.00  54.00 116.28  114
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0918221000
_diffrn_orient_matrix_UB_12      0.0089692000
_diffrn_orient_matrix_UB_13      0.0441793000
_diffrn_orient_matrix_UB_21      0.0359116000
_diffrn_orient_matrix_UB_22      0.0575450000
_diffrn_orient_matrix_UB_23      -0.0208263000
_diffrn_orient_matrix_UB_31      -0.0105639000
_diffrn_orient_matrix_UB_32      0.0498657000
_diffrn_orient_matrix_UB_33      0.0555857000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4087
_reflns_number_total             4355
_reflns_odcompleteness_completeness 95.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.972
_refine_diff_density_min         -0.674
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         4355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0217
_refine_ls_R_factor_gt           0.0197
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0290P)²+0.2186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0527
_refine_ls_wR_factor_ref         0.0533
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C2'(H2'), C3'(H3'), C5'(H5'), C6'(H6')
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C8'(H8'A,H8'B,H8'C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.15086(2) 0.41239(2) 0.36276(2) 0.02478(4) Uani 1 1 d . . . . .
C1 C 0.4322(2) 0.69769(16) 0.40932(15) 0.0177(3) Uani 1 1 d . . . . .
C2 C 0.3660(2) 0.54921(16) 0.33385(16) 0.0189(3) Uani 1 1 d . . . . .
C3 C 0.4469(2) 0.48683(17) 0.24432(16) 0.0203(3) Uani 1 1 d . . . . .
H3 H 0.400609 0.388035 0.194390 0.024 Uiso 1 1 calc R . . . .
C4 C 0.5976(2) 0.57300(17) 0.22975(16) 0.0192(3) Uani 1 1 d . . . . .
C5 C 0.6640(2) 0.72140(17) 0.30199(16) 0.0197(3) Uani 1 1 d . . . . .
H5 H 0.762937 0.779338 0.290783 0.024 Uiso 1 1 calc R . . . .
C6 C 0.5818(2) 0.78216(17) 0.39060(16) 0.0198(3) Uani 1 1 d . . . . .
H6 H 0.626960 0.881304 0.438825 0.024 Uiso 1 1 calc R . . . .
C7 C 0.6966(2) 0.51208(18) 0.14043(16) 0.0223(3) Uani 1 1 d . . . . .
C8 C 0.7125(3) 0.3001(2) -0.0067(2) 0.0334(4) Uani 1 1 d . . . . .
H8A H 0.722807 0.345809 -0.073561 0.050 Uiso 1 1 calc GR . . . .
H8B H 0.641586 0.199798 -0.054711 0.050 Uiso 1 1 calc GR . . . .
H8C H 0.835173 0.308646 0.053091 0.050 Uiso 1 1 calc GR . . . .
C1' C 0.3572(2) 0.76901(16) 0.51120(15) 0.0176(3) Uani 1 1 d . . . . .
C2' C 0.4683(2) 0.82474(18) 0.65321(17) 0.0217(3) Uani 1 1 d . . . . .
H2' H 0.587278 0.815339 0.682613 0.026 Uiso 1 1 calc R . . . .
C3' C 0.4033(2) 0.89388(17) 0.75080(16) 0.0215(3) Uani 1 1 d . . . . .
H3' H 0.476366 0.927330 0.845399 0.026 Uiso 1 1 calc R . . . .
C4' C 0.2290(2) 0.91299(16) 0.70691(15) 0.0182(3) Uani 1 1 d . . . . .
C5' C 0.1172(2) 0.85905(17) 0.56502(16) 0.0196(3) Uani 1 1 d . . . . .
H5' H 0.000459 0.872312 0.535670 0.023 Uiso 1 1 calc R . . . .
C6' C 0.1799(2) 0.78578(17) 0.46792(16) 0.0198(3) Uani 1 1 d . . . . .
H6' H 0.103877 0.747738 0.373798 0.024 Uiso 1 1 calc R . . . .
C7' C 0.1654(2) 0.99246(17) 0.81339(16) 0.0205(3) Uani 1 1 d . . . . .
C8' C -0.0647(3) 1.0959(2) 0.8513(2) 0.0304(4) Uani 1 1 d . . . . .
H8'A H -0.175166 1.113332 0.800161 0.046 Uiso 1 1 calc GR . . . .
H8'B H 0.028673 1.186443 0.911708 0.046 Uiso 1 1 calc GR . . . .
H8'C H -0.094534 1.039635 0.906174 0.046 Uiso 1 1 calc GR . . . .
O1 O 0.61933(19) 0.36961(14) 0.07604(14) 0.0300(3) Uani 1 1 d . . . . .
O2 O 0.83127(19) 0.58307(14) 0.12953(14) 0.0338(3) Uani 1 1 d . . . . .
O1' O 0.00594(17) 1.01787(13) 0.75496(12) 0.0248(2) Uani 1 1 d . . . . .
O2' O 0.24801(19) 1.03083(16) 0.93741(13) 0.0317(3) 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 2.1044(15) . ?
C1 C2 1.399(2) . ?
C1 C6 1.401(2) . ?
C1 C1' 1.484(2) . ?
C2 C3 1.389(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.392(2) . ?
C4 C5 1.392(2) . ?
C4 C7 1.494(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(2) . ?
C6 H6 0.9300 . ?
C7 O1 1.333(2) . ?
C7 O2 1.205(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 O1 1.445(2) . ?
C1' C2' 1.397(2) . ?
C1' C6' 1.397(2) . ?
C2' H2' 0.9300 . ?
C2' C3' 1.386(2) . ?
C3' H3' 0.9300 . ?
C3' C4' 1.386(2) . ?
C4' C5' 1.397(2) . ?
C4' C7' 1.489(2) . ?
C5' H5' 0.9300 . ?
C5' C6' 1.386(2) . ?
C6' H6' 0.9300 . ?
C7' O1' 1.338(2) . ?
C7' O2' 1.2037(19) . ?
C8' H8'A 0.9600 . ?
C8' H8'B 0.9600 . ?
C8' H8'C 0.9600 . ?
C8' O1' 1.445(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
C2 C1 C6 117.83(14) . . ?
C2 C1 C1' 123.58(14) . . ?
C6 C1 C1' 118.55(13) . . ?
C1 C2 I1 120.47(11) . . ?
C3 C2 I1 118.16(11) . . ?
C3 C2 C1 121.27(14) . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.63(14) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.16(14) . . ?
C3 C4 C7 122.42(14) . . ?
C5 C4 C7 117.41(14) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.57(14) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 H6 119.2 . . ?
C5 C6 C1 121.51(14) . . ?
C5 C6 H6 119.2 . . ?
O1 C7 C4 111.76(14) . . ?
O2 C7 C4 123.96(15) . . ?
O2 C7 O1 124.27(15) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
C2' C1' C1 119.37(14) . . ?
C6' C1' C1 121.43(13) . . ?
C6' C1' C2' 119.17(14) . . ?
C1' C2' H2' 119.6 . . ?
C3' C2' C1' 120.75(15) . . ?
C3' C2' H2' 119.6 . . ?
C2' C3' H3' 120.1 . . ?
C4' C3' C2' 119.76(14) . . ?
C4' C3' H3' 120.1 . . ?
C3' C4' C5' 120.04(14) . . ?
C3' C4' C7' 118.71(14) . . ?
C5' C4' C7' 121.25(14) . . ?
C4' C5' H5' 119.9 . . ?
C6' C5' C4' 120.11(14) . . ?
C6' C5' H5' 119.9 . . ?
C1' C6' H6' 119.9 . . ?
C5' C6' C1' 120.12(14) . . ?
C5' C6' H6' 119.9 . . ?
O1' C7' C4' 111.96(13) . . ?
O2' C7' C4' 124.27(15) . . ?
O2' C7' O1' 123.77(15) . . ?
H8'A C8' H8'B 109.5 . . ?
H8'A C8' H8'C 109.5 . . ?
H8'B C8' H8'C 109.5 . . ?
O1' C8' H8'A 109.5 . . ?
O1' C8' H8'B 109.5 . . ?
O1' C8' H8'C 109.5 . . ?
C7 O1 C8 115.57(15) . . ?
C7' O1' C8' 115.49(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
I1 C2 C3 C4 -175.86(11) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C1 C1' C2' C3' 179.04(15) . . . . ?
C1 C1' C6' C5' -176.89(14) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
C2 C1 C1' C2' 110.65(18) . . . . ?
C2 C1 C1' C6' -71.4(2) . . . . ?
C2 C3 C4 C5 -1.5(2) . . . . ?
C2 C3 C4 C7 177.14(14) . . . . ?
C3 C4 C5 C6 1.4(2) . . . . ?
C3 C4 C7 O1 1.8(2) . . . . ?
C3 C4 C7 O2 -177.31(16) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
C4 C7 O1 C8 -176.71(14) . . . . ?
C5 C4 C7 O1 -179.52(14) . . . . ?
C5 C4 C7 O2 1.4(2) . . . . ?
C6 C1 C2 I1 176.94(11) . . . . ?
C6 C1 C2 C3 0.7(2) . . . . ?
C6 C1 C1' C2' -67.1(2) . . . . ?
C6 C1 C1' C6' 110.87(17) . . . . ?
C7 C4 C5 C6 -177.34(14) . . . . ?
C1' C1 C2 I1 -0.8(2) . . . . ?
C1' C1 C2 C3 -177.05(14) . . . . ?
C1' C1 C6 C5 177.02(14) . . . . ?
C1' C2' C3' C4' -2.5(2) . . . . ?
C2' C1' C6' C5' 1.1(2) . . . . ?
C2' C3' C4' C5' 1.8(2) . . . . ?
C2' C3' C4' C7' -177.73(14) . . . . ?
C3' C4' C5' C6' 0.3(2) . . . . ?
C3' C4' C7' O1' 172.37(14) . . . . ?
C3' C4' C7' O2' -6.9(2) . . . . ?
C4' C5' C6' C1' -1.7(2) . . . . ?
C4' C7' O1' C8' -179.48(13) . . . . ?
C5' C4' C7' O1' -7.2(2) . . . . ?
C5' C4' C7' O2' 173.54(16) . . . . ?
C6' C1' C2' C3' 1.0(2) . . . . ?
C7' C4' C5' C6' 179.81(14) . . . . ?
O2 C7 O1 C8 2.4(2) . . . . ?
O2' C7' O1' C8' -0.2(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'Mitegen mount + Paratone'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.425
_oxdiff_exptl_absorpt_empirical_full_min 0.839
####################################################################### 
# 
# 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_exp_81mrb3
_database_code_depnum_ccdc_archive 'CCDC 1953895'
loop_
_audit_author_name
_audit_author_address
'Christopher Richardson'
;University of Wollongong
Australia
;
_audit_update_record             
;
2019-09-16 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-08-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
"2-iodo-[1,1'-biphenyl]-4,4'-dicarboxylic acid dimethylsulfoxide solvate"
_chemical_formula_moiety         'C14 H9 I O4, C2 H6 O S'
_chemical_formula_sum            'C16 H15 I O5 S'
_chemical_formula_weight         446.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H15IO5S
_chemical_oxdiff_usercomment     'crystallised from DMSO solution'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.19869(18)
_cell_length_b                   8.27594(19)
_cell_length_c                   13.9191(2)
_cell_angle_alpha                86.9929(16)
_cell_angle_beta                 74.1903(17)
_cell_angle_gamma                69.153(2)
_cell_volume                     848.18(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9827
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.5960
_cell_measurement_theta_min      2.6220
_shelx_estimated_absorpt_T_max   0.838
_shelx_estimated_absorpt_T_min   0.512
_exptl_absorpt_coefficient_mu    2.032
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       wedge
_exptl_crystal_F_000             440
_exptl_crystal_recrystallization_method 'slow evaporation from DMSO'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16754
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.703
_diffrn_reflns_theta_min         2.637
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'HyPix Bantam HPC-3000'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     45.00  71.00   0.50    7.00    --   20.00  54.00  30.00   52
  2  ω    -73.00  -7.00   0.50    7.00    --   20.00  54.00 -90.00  132
  3  ω     40.00  97.00   0.50    7.00    --   20.00  54.00 -90.00  114
  4  ω    -74.00  87.00   0.50    7.00    --   20.00  54.00 150.00  322
  5  ω    -69.00  42.00   0.50    7.00    --   20.00  54.00-150.00  222
  6  ω    -71.00 109.00   0.50    7.00    --   20.00  54.00  60.00  360
  7  ω    -68.00  68.00   0.50    7.00    --   20.00  54.00 120.00  272
  8  ω    -73.00 -26.00   0.50    7.00    --   20.00  54.00   0.00   94
  9  ω     75.00 100.00   0.50    7.00    --   20.00  54.00   0.00   50
 10  ω    -62.00 -36.00   0.50    7.00    --   20.00  54.00  90.00   52
 11  ω    -21.00  64.00   0.50    7.00    --   20.00  54.00  90.00  170
 12  ω    -66.00   3.00   0.50    7.00    --   20.00  54.00-120.00  138
 13  ω    -26.00  -1.00   0.50    7.00    --   20.00  54.00-180.00   50
 14  ω      6.00  56.00   0.50    7.00    --   20.00  54.00-180.00  100
 15  ω    -66.00 -15.00   0.50    7.00    --   20.00  54.00  30.00  102
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0252457000
_diffrn_orient_matrix_UB_12      -0.0101664000
_diffrn_orient_matrix_UB_13      -0.0528977000
_diffrn_orient_matrix_UB_21      -0.0633443000
_diffrn_orient_matrix_UB_22      0.0839234000
_diffrn_orient_matrix_UB_23      -0.0022959000
_diffrn_orient_matrix_UB_31      0.0678566000
_diffrn_orient_matrix_UB_32      0.0358463000
_diffrn_orient_matrix_UB_33      -0.0029052000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4151
_reflns_number_total             4989
_reflns_odcompleteness_completeness 95.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.593
_refine_diff_density_min         -1.393
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4989
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0262
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0317P)²+0.5050P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0640
_refine_ls_wR_factor_ref         0.0676
_refine_special_details          
;The hydrogen atom of the carboxylic acid were modelled as correlated 
disorder together with the disordered DMSO molecule.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Rigid body (RIGU) restrains
 S2, O5, C8, H8A, H8B, H8C, C9, H9A, H9B, H9C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S1, O6, C10, H10A, H10B, H10C, C11, H11A, H11B, H11C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(S1)=Sof(O6)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=Sof(C11)=Sof(H11A)=
 Sof(H11B)=Sof(H11C)=Sof(H2)=1-FVAR(1)
 Sof(S2)=Sof(O5)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(C9)=Sof(H9A)=Sof(H9B)=
 Sof(H9C)=Sof(H1)=FVAR(1)
4.a Free rotating group:
 S1(O6,C10,H10A,H10B,H10C,C11,H11A,H11B,H11C), S2(O5,C8,H8A,H8B,H8C,C9,H9A,H9B,
 H9C)
4.b Aromatic/amide H refined with riding coordinates:
 C2'(H2'), C3(H3), C3'(H3'), C5(H5), C5'(H5'), C6(H6), C6'(H6')
4.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.16702(3) 0.03280(2) 0.61320(2) 0.04759(7) Uani 1 1 d . . . . .
S1 S 0.1031(2) 0.18504(15) -0.01020(8) 0.0306(3) Uani 0.544(3) 1 d . U P A 2
O6 O 0.1760(4) 0.3205(3) 0.00692(19) 0.0475(9) Uani 0.544(3) 1 d G U P A 2
C10 C 0.0208(6) 0.2417(5) -0.1200(2) 0.052(2) Uani 0.544(3) 1 d G U P A 2
H10A H 0.126399 0.262996 -0.180686 0.030(14) Uiso 0.544(3) 1 d G U P A 2
H10B H -0.019872 0.139660 -0.141024 0.24(7) Uiso 0.544(3) 1 d G U P A 2
H10C H -0.096368 0.361317 -0.100450 0.069(18) Uiso 0.544(3) 1 d G U P A 2
C11 C 0.2967(4) -0.0043(3) -0.0671(4) 0.0502(13) Uani 0.544(3) 1 d G U P A 2
H11A H 0.251357 -0.102102 -0.089050 0.063(19) Uiso 0.544(3) 1 d G U P A 2
H11B H 0.383897 0.033494 -0.131320 0.16(4) Uiso 0.544(3) 1 d G U P A 2
H11C H 0.369932 -0.054266 -0.011063 0.078(19) Uiso 0.544(3) 1 d G U P A 2
S2 S 0.1927(2) 0.16087(16) -0.03615(10) 0.0268(3) Uani 0.456(3) 1 d . U P A 1
O5 O 0.0976(4) 0.1024(3) 0.05964(12) 0.0320(8) Uani 0.456(3) 1 d G U P A 1
C8 C 0.3257(6) -0.0308(3) -0.1177(2) 0.0507(18) Uani 0.456(3) 1 d G U P A 1
H8A H 0.239280 -0.102976 -0.121771 0.12(4) Uiso 0.456(3) 1 d G U P A 1
H8B H 0.385834 0.005573 -0.191658 0.09(3) Uiso 0.456(3) 1 d G U P A 1
H8C H 0.432418 -0.108875 -0.084443 0.07(2) Uiso 0.456(3) 1 d G U P A 1
C9 C 0.0267(4) 0.2533(7) -0.1058(2) 0.0206(11) Uani 0.456(3) 1 d G U P A 1
H9A H 0.092051 0.284716 -0.179914 0.13(5) Uiso 0.456(3) 1 d G U P A 1
H9B H -0.039654 0.162046 -0.110668 0.021(12) Uiso 0.456(3) 1 d G U P A 1
H9C H -0.072671 0.371057 -0.064280 0.07(2) Uiso 0.456(3) 1 d G U P A 1
O1 O 0.1627(2) 0.13182(18) 0.22331(10) 0.0313(3) Uani 1 1 d . . . . .
H1 H 0.137625 0.137217 0.168321 0.047 Uiso 0.456(3) 1 calc GR . P . .
O2 O 0.2401(2) 0.3599(2) 0.16777(10) 0.0354(3) Uani 1 1 d . . . . .
H2 H 0.208592 0.341440 0.118042 0.053 Uiso 0.544(3) 1 calc GR . P . .
O3 O 0.35740(19) 0.58961(17) 0.93382(10) 0.0281(3) Uani 1 1 d . . . . .
O4 O 0.57638(19) 0.32863(17) 0.90466(11) 0.0297(3) Uani 1 1 d . . . . .
H4 H 0.597545 0.358606 0.955370 0.045 Uiso 1 1 calc GR . . . .
C1 C 0.2753(2) 0.3407(2) 0.52232(12) 0.0208(3) Uani 1 1 d . . . . .
C1' C 0.3164(2) 0.3673(2) 0.61665(12) 0.0203(3) Uani 1 1 d . . . . .
C2 C 0.2269(2) 0.2020(2) 0.50288(12) 0.0226(3) Uani 1 1 d . . . . .
C2' C 0.4495(2) 0.2376(2) 0.64958(13) 0.0237(3) Uani 1 1 d . . . . .
H2' H 0.510635 0.129337 0.612994 0.028 Uiso 1 1 calc R . . . .
C3 C 0.2033(2) 0.1768(2) 0.41043(13) 0.0229(3) Uani 1 1 d . . . . .
H3 H 0.170658 0.081943 0.398535 0.027 Uiso 1 1 calc R . . . .
C3' C 0.4941(2) 0.2647(2) 0.73533(13) 0.0223(3) Uani 1 1 d . . . . .
H3' H 0.587331 0.176734 0.756291 0.027 Uiso 1 1 calc R . . . .
C4 C 0.2273(2) 0.2902(2) 0.33545(12) 0.0209(3) Uani 1 1 d . . . . .
C4' C 0.4008(2) 0.4221(2) 0.79031(12) 0.0202(3) Uani 1 1 d . . . . .
C5 C 0.2656(3) 0.4335(2) 0.35486(13) 0.0259(4) Uani 1 1 d . . . . .
H5 H 0.274964 0.515257 0.305086 0.031 Uiso 1 1 calc R . . . .
C5' C 0.2690(2) 0.5521(2) 0.75753(13) 0.0232(3) Uani 1 1 d . . . . .
H5' H 0.205828 0.659449 0.794923 0.028 Uiso 1 1 calc R . . . .
C6 C 0.2900(2) 0.4572(2) 0.44714(13) 0.0246(3) Uani 1 1 d . . . . .
H6 H 0.317468 0.555117 0.459481 0.030 Uiso 1 1 calc R . . . .
C6' C 0.2291(2) 0.5258(2) 0.67039(13) 0.0228(3) Uani 1 1 d . . . . .
H6' H 0.141600 0.616730 0.647149 0.027 Uiso 1 1 calc R . . . .
C7 C 0.2090(2) 0.2578(3) 0.23473(13) 0.0260(4) Uani 1 1 d . . . . .
C7' C 0.4420(2) 0.4546(2) 0.88325(13) 0.0222(3) 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 2.1006(17) . ?
S1 O6 1.5015 . ?
S1 C10 1.8098 . ?
S1 C11 1.8104 . ?
C10 H10A 1.0900 . ?
C10 H10B 1.0902 . ?
C10 H10C 1.0889 . ?
C11 H11A 1.0904 . ?
C11 H11B 1.0900 . ?
C11 H11C 1.0887 . ?
S2 O5 1.5016 . ?
S2 C8 1.8102 . ?
S2 C9 1.8104 . ?
C8 H8A 1.0901 . ?
C8 H8B 1.0906 . ?
C8 H8C 1.0886 . ?
C9 H9A 1.0903 . ?
C9 H9B 1.0902 . ?
C9 H9C 1.0888 . ?
O1 H1 0.8400 . ?
O1 C7 1.260(2) . ?
O2 H2 0.8400 . ?
O2 C7 1.261(2) . ?
O3 C7' 1.221(2) . ?
O4 H4 0.8400 . ?
O4 C7' 1.310(2) . ?
C1 C1' 1.487(2) . ?
C1 C2 1.401(2) . ?
C1 C6 1.396(2) . ?
C1' C2' 1.393(2) . ?
C1' C6' 1.391(2) . ?
C2 C3 1.389(2) . ?
C2' H2' 0.9500 . ?
C2' C3' 1.390(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(2) . ?
C3' H3' 0.9500 . ?
C3' C4' 1.394(2) . ?
C4 C5 1.387(3) . ?
C4 C7 1.498(2) . ?
C4' C5' 1.387(2) . ?
C4' C7' 1.483(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(2) . ?
C5' H5' 0.9500 . ?
C5' C6' 1.385(2) . ?
C6 H6 0.9500 . ?
C6' H6' 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 S1 C10 106.9 . . ?
O6 S1 C11 106.9 . . ?
C10 S1 C11 96.4 . . ?
S1 C10 H10A 109.2 . . ?
S1 C10 H10B 110.0 . . ?
S1 C10 H10C 106.9 . . ?
H10A C10 H10B 111.2 . . ?
H10A C10 H10C 109.6 . . ?
H10B C10 H10C 109.7 . . ?
S1 C11 H11A 110.0 . . ?
S1 C11 H11B 109.3 . . ?
S1 C11 H11C 107.0 . . ?
H11A C11 H11B 111.2 . . ?
H11A C11 H11C 109.7 . . ?
H11B C11 H11C 109.6 . . ?
O5 S2 C8 106.9 . . ?
O5 S2 C9 106.9 . . ?
C8 S2 C9 96.3 . . ?
S2 C8 H8A 109.2 . . ?
S2 C8 H8B 110.0 . . ?
S2 C8 H8C 107.0 . . ?
H8A C8 H8B 111.2 . . ?
H8A C8 H8C 109.6 . . ?
H8B C8 H8C 109.7 . . ?
S2 C9 H9A 110.0 . . ?
S2 C9 H9B 109.3 . . ?
S2 C9 H9C 107.0 . . ?
H9A C9 H9B 111.2 . . ?
H9A C9 H9C 109.7 . . ?
H9B C9 H9C 109.6 . . ?
C7 O1 H1 109.5 . . ?
C7 O2 H2 109.5 . . ?
C7' O4 H4 109.5 . . ?
C2 C1 C1' 123.82(15) . . ?
C6 C1 C1' 118.64(15) . . ?
C6 C1 C2 117.52(15) . . ?
C2' C1' C1 120.60(15) . . ?
C6' C1' C1 120.28(15) . . ?
C6' C1' C2' 119.02(15) . . ?
C1 C2 I1 122.52(12) . . ?
C3 C2 I1 116.18(13) . . ?
C3 C2 C1 121.15(16) . . ?
C1' C2' H2' 119.6 . . ?
C3' C2' C1' 120.80(16) . . ?
C3' C2' H2' 119.6 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.01(16) . . ?
C4 C3 H3 120.0 . . ?
C2' C3' H3' 120.3 . . ?
C2' C3' C4' 119.43(16) . . ?
C4' C3' H3' 120.3 . . ?
C3 C4 C7 119.58(16) . . ?
C5 C4 C3 119.74(15) . . ?
C5 C4 C7 120.67(16) . . ?
C3' C4' C7' 121.00(15) . . ?
C5' C4' C3' 120.00(15) . . ?
C5' C4' C7' 118.99(15) . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.81(16) . . ?
C6 C5 H5 120.1 . . ?
C4' C5' H5' 119.9 . . ?
C6' C5' C4' 120.16(16) . . ?
C6' C5' H5' 119.9 . . ?
C1 C6 H6 119.2 . . ?
C5 C6 C1 121.61(16) . . ?
C5 C6 H6 119.2 . . ?
C1' C6' H6' 119.7 . . ?
C5' C6' C1' 120.50(16) . . ?
C5' C6' H6' 119.7 . . ?
O1 C7 O2 124.91(17) . . ?
O1 C7 C4 117.87(17) . . ?
O2 C7 C4 117.22(17) . . ?
O3 C7' O4 123.80(16) . . ?
O3 C7' C4' 121.66(15) . . ?
O4 C7' C4' 114.53(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O4 H4 O3 0.84 1.79 2.6255(18) 176.6 2_667 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C2 C3 C4 175.47(13) . . . . ?
C1 C1' C2' C3' 177.09(16) . . . . ?
C1 C1' C6' C5' -179.02(16) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C1' C1 C2 I1 9.6(2) . . . . ?
C1' C1 C2 C3 -175.13(17) . . . . ?
C1' C1 C6 C5 175.61(17) . . . . ?
C1' C2' C3' C4' 1.7(3) . . . . ?
C2 C1 C1' C2' 55.5(2) . . . . ?
C2 C1 C1' C6' -128.05(19) . . . . ?
C2 C1 C6 C5 -2.7(3) . . . . ?
C2 C3 C4 C5 -3.4(3) . . . . ?
C2 C3 C4 C7 177.52(16) . . . . ?
C2' C1' C6' C5' -2.5(3) . . . . ?
C2' C3' C4' C5' -2.1(3) . . . . ?
C2' C3' C4' C7' 178.82(16) . . . . ?
C3 C4 C5 C6 3.8(3) . . . . ?
C3 C4 C7 O1 3.6(2) . . . . ?
C3 C4 C7 O2 -176.88(17) . . . . ?
C3' C4' C5' C6' 0.2(3) . . . . ?
C3' C4' C7' O3 -177.59(18) . . . . ?
C3' C4' C7' O4 3.3(2) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C4' C5' C6' C1' 2.1(3) . . . . ?
C5 C4 C7 O1 -175.52(17) . . . . ?
C5 C4 C7 O2 4.0(3) . . . . ?
C5' C4' C7' O3 3.4(3) . . . . ?
C5' C4' C7' O4 -175.76(17) . . . . ?
C6 C1 C1' C2' -122.72(19) . . . . ?
C6 C1 C1' C6' 53.7(2) . . . . ?
C6 C1 C2 I1 -172.18(13) . . . . ?
C6 C1 C2 C3 3.1(3) . . . . ?
C6' C1' C2' C3' 0.6(3) . . . . ?
C7 C4 C5 C6 -177.14(16) . . . . ?
C7' C4' C5' C6' 179.32(16) . . . . ?

_olex2_exptl_crystal_mounting_method 'Mitegenmount + Paratone'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.497
_oxdiff_exptl_absorpt_empirical_full_min 0.861
