# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_C6ICl5
_database_code_depnum_ccdc_archive 'CCDC 2106689'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2021-08-31 deposited with the CCDC.	2021-11-22 downloaded from the CCDC.
;

_audit_creation_date             2021-06-22
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
EricBosch@MissouriState.edu
daniel.unruh@ttu.edu
''
' ryangroeneman19@webster.edu'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 Cl5 I1'
_chemical_formula_sum            'C6 Cl5 I'
_chemical_formula_weight         376.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12  Cl10  I2  '
_chemical_oxdiff_usercomment     'vial 4'
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'
Cl Cl 0.3639 0.7018 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.1229(2)
_cell_length_b                   3.91380(10)
_cell_length_c                   15.0718(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.013(2)
_cell_angle_gamma                90
_cell_volume                     478.86(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5231
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.7300
_cell_measurement_theta_min      5.7960
_shelx_estimated_absorpt_T_max   0.381
_shelx_estimated_absorpt_T_min   0.140
_exptl_absorpt_coefficient_mu    38.608
_exptl_absorpt_correction_T_max  0.535
_exptl_absorpt_correction_T_min  0.168
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.609
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             348
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 0 -1 0.0135
2 -2 1 0.0376
2 0 1 0.0176
2 2 1 0.0285
-4 0 7 0.0118
4 -1 -5 0.0187
0 -2 7 0.0371
0 0 -10 0.0077
0 -1 10 0.0226
-2 -1 -7 0.0227

_exptl_crystal_size_max          0.084
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.031
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.9978 -0.0004 -1.0024 0.3216 -0.0909 -0.2128
1.9951 -1.9969 0.9972 0.0978 0.0198 0.8740
1.9978 0.0004 1.0024 -0.3216 0.0909 0.2128
2.0004 1.9977 1.0076 -0.7409 0.1620 -0.4484
-3.6312 0.3783 7.1750 0.0744 -0.9429 -0.3248
3.9315 -1.0334 -5.4209 -0.0622 0.7921 0.6072
0.0335 -1.8261 6.7930 0.0531 -0.6596 0.7497
0.1555 0.1359 -9.7694 0.4179 0.8779 -0.2337
0.3432 -0.5254 9.5225 -0.3927 -0.8254 0.4055
-1.5139 -1.4329 -7.4719 0.8653 0.4703 0.1733

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6562
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.974
_diffrn_reflns_theta_min         5.875
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -46.00  24.00   0.50    0.34    --  -47.91  43.00-113.00  140
  2  ω   -120.00 -34.00   0.50    0.34    --  -47.91 -43.00  94.00  172
  3  ω     36.00 120.00   0.50    0.34    --   47.91  43.00-113.00  168
  4  ω    -24.00  50.00   0.50    0.34    --   47.91 -43.00  94.00  148
  5  ω   -164.00 -78.00   0.50    1.35    --  -91.75 -43.00  94.00  172
  6  ω    -46.00 -19.00   0.50    1.35    --  -91.75  43.00-113.00   54
  7  ω     94.00 178.00   0.50    1.35    --  107.78  43.00-113.00  168
  8  ω   -119.00 -25.00   0.50    0.34    --  -47.91 -77.00  30.00  188
  9  ω    -24.00  28.00   0.50    0.34    --  -47.91  19.00  30.00  104
 10  ω    -24.00  28.00   0.50    0.34    --  -47.91  19.00-120.00  104
 11  ω   -163.00 -77.00   0.50    1.35    --  -91.75 -56.00 -44.46  172
 12  ω   -163.00 -69.00   0.50    1.35    --  -91.75 -77.00  30.00  188
 13  ω   -163.00 -69.00   0.50    1.35    --  -91.75 -76.00  41.73  188
 14  ω   -163.00 -78.00   0.50    1.35    --  -91.75 -50.00 -20.92  170
 15  ω    -64.00 -19.00   0.50    1.35    --  -91.75  57.00  60.00   90
 16  ω   -163.00 -77.00   0.50    1.35    --  -91.75 -54.00  -6.62  172
 17  ω   -163.00 -77.00   0.50    1.35    --  -91.75 -55.00 -38.84  172
 18  ω   -103.00 -19.00   0.50    1.35    --  -91.75  77.00  90.00  168
 19  ω   -163.00 -69.00   0.50    1.35    --  -91.75 -77.00   0.00  188
 20  ω   -163.00 -77.00   0.50    1.35    --  -91.75 -57.00  60.00  172
 21  ω    -64.00 -19.00   0.50    1.35    --  -91.75  57.00  90.00   90
 22  ω    -64.00 -19.00   0.50    1.35    --  -91.75  57.00   0.00   90
 23  ω   -163.00 -76.00   0.50    1.35    --  -91.75 -60.00 -11.47  174
 24  ω     35.00  68.00   0.50    1.35    --  107.78 -57.00 -60.00   66
 25  ω     35.00  68.00   0.50    1.35    --  107.78 -57.00  90.00   66
 26  ω     35.00 106.00   0.50    1.35    --  107.78 -99.00-180.00  142
 27  ω     35.00 106.00   0.50    1.35    --  107.78 -99.00 150.00  142
 28  ω     35.00 106.00   0.50    1.35    --  107.78 -99.00 -90.00  142
 29  ω     35.00 107.00   0.50    1.35    --  107.78 -77.00-180.00  144
 30  ω   -119.00 -73.00   0.50    0.34    --  -47.91-125.00-180.00   92
 31  ω   -119.00 -33.00   0.50    0.34    --  -47.91 -57.00-120.00  172
 32  ω   -119.00 -33.00   0.50    0.34    --  -47.91 -57.00  90.00  172
 33  ω     25.00 121.00   0.50    0.34    --   47.91  77.00 -60.00  192
 34  ω     25.00 121.00   0.50    0.34    --   47.91  77.00 150.00  192
 35  ω   -163.00-132.00   0.50    1.35    --  -91.75 -73.00 161.00   62
 36  ω     95.00 178.00   0.50    1.35    --  107.78  19.00-180.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1369145000
_diffrn_orient_matrix_UB_12      -0.2096482000
_diffrn_orient_matrix_UB_13      -0.0478673000
_diffrn_orient_matrix_UB_21      0.0896060000
_diffrn_orient_matrix_UB_22      0.0357145000
_diffrn_orient_matrix_UB_23      -0.0879417000
_diffrn_orient_matrix_UB_31      0.0961285000
_diffrn_orient_matrix_UB_32      -0.3312422000
_diffrn_orient_matrix_UB_33      0.0208488000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                892
_reflns_number_total             946
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       0.0013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         946
_refine_ls_number_restraints     44
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0260
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0298P)²+0.7779P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0674
_refine_special_details          
'The iodine position was disordered over three sites. To help maintain reasonable ADP values for the minor iodine sites, bond lengths, and the correct chemical formula constraints and restraints were applied. The EADP constraint was applied to the I2:Cl1 and I3:Cl2 atom pairs. Free variable DFIX restraints were applied to all C-Cl and C-I bond lengths. The rigid bond restraint RIGU was all applied to all atoms in the structure as well.'
_olex2_refinement_description    
;
1. Restrained distances
 C1-Cl3 = C3-Cl2 = C2-Cl1
 1.74392 with sigma of 0.02
 C1-I1 = C2-I2 = C3-I3
 1.93416 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
Uanis(Cl1) = Uanis(I2)
Uanis(Cl2) = Uanis(I3)
3. Rigid body (RIGU) restrains
 C1, C2, C3, I1, I2, I3, Cl1, Cl2, Cl3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 1*[Sof(I1)+Sof(Cl3)]+1*[Sof(Cl1)+Sof(I2)]+1*[Sof(Cl2)+Sof(I3)]=0.5 with esd
 of 0
 Sof(Cl3)=1-FVAR(1)
 Sof(I1)=FVAR(1)
 Sof(Cl1)=1-FVAR(2)
 Sof(I2)=FVAR(2)
 Sof(Cl2)=1-FVAR(3)
 Sof(I3)=FVAR(3)
;
_atom_sites_solution_hydrogens   .
_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 0.7836(5) 0.1612(13) 0.6447(3) 0.0246(4) Uani 0.3744(13) 1 d D . P A 1
Cl1 Cl 0.4156(10) 0.394(3) 0.6992(4) 0.0370(5) Uani 0.9280(13) 1 d D . P B 1
Cl2 Cl 0.8398(4) 0.2577(18) 0.4324(4) 0.0361(5) Uani 0.9464(13) 1 d D . P C 1
Cl3 Cl 0.7594(12) 0.154(3) 0.6332(7) 0.0306(15) Uani 0.6256(13) 1 d D . P A 2
I2 I 0.406(4) 0.383(10) 0.7086(14) 0.0370(5) Uani 0.0720(13) 1 d D . P B 2
I3 I 0.863(2) 0.254(10) 0.430(2) 0.0361(5) Uani 0.0536(13) 1 d D . P C 2
C1 C 0.6154(4) 0.3504(9) 0.5588(2) 0.0279(7) Uani 1 1 d D . . . .
C2 C 0.4632(4) 0.4546(9) 0.5890(2) 0.0285(7) Uani 1 1 d D . . . .
C3 C 0.6522(4) 0.3942(9) 0.4698(2) 0.0284(7) Uani 1 1 d 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 1.992(6) . ?
Cl1 C2 1.735(6) . ?
Cl2 C3 1.727(5) . ?
Cl3 C1 1.769(10) . ?
I2 C2 1.899(18) . ?
I3 C3 1.912(18) . ?
C1 C2 1.393(5) . ?
C1 C3 1.395(5) . ?
C2 C3 1.398(5) 3_666 ?

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 I1 119.5(3) . . ?
C2 C1 Cl3 119.7(4) . . ?
C2 C1 C3 120.0(3) . . ?
C3 C1 I1 120.3(3) . . ?
C3 C1 Cl3 120.3(4) . . ?
C1 C2 Cl1 120.2(4) . . ?
C1 C2 I2 121.2(10) . . ?
C1 C2 C3 120.0(3) . 3_666 ?
C3 C2 Cl1 119.8(4) 3_666 . ?
C3 C2 I2 118.8(10) 3_666 . ?
C1 C3 Cl2 119.8(3) . . ?
C1 C3 I3 119.4(11) . . ?
C1 C3 C2 120.0(3) . 3_666 ?
C2 C3 Cl2 120.2(3) 3_666 . ?
C2 C3 I3 120.6(11) 3_666 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C1 C2 Cl1 -4.1(6) . . . . ?
I1 C1 C2 C3 176.3(3) . . . 3_666 ?
I1 C1 C3 Cl2 4.3(5) . . . . ?
I1 C1 C3 C2 -176.3(3) . . . 3_666 ?
Cl3 C1 C2 I2 -1.0(15) . . . . ?
Cl3 C1 C2 C3 -179.1(5) . . . 3_666 ?
Cl3 C1 C3 I3 -2.1(14) . . . . ?
Cl3 C1 C3 C2 179.1(5) . . . 3_666 ?
C2 C1 C3 Cl2 -178.9(4) . . . . ?
C2 C1 C3 I3 179.4(13) . . . . ?
C2 C1 C3 C2 0.6(6) . . . 3_666 ?
C3 C1 C2 Cl1 179.0(5) . . . . ?
C3 C1 C2 I2 177.5(14) . . . . ?
C3 C1 C2 C3 -0.6(6) . . . 3_666 ?

_olex2_exptl_crystal_mounting_method 'Hampton Research 20 micron nylon CryoLoop'
_olex2_submission_original_sample_id gro21_23
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   284
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.507
_oxdiff_exptl_absorpt_empirical_full_min 0.657
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
####################################################################### 
# 
# 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_C6ICl5_BPA
_database_code_depnum_ccdc_archive 'CCDC 2106691'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2021-08-31 deposited with the CCDC.	2021-11-22 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT911_C6ICl5_BPA          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         11 Report
RESPONSE: These reflections were omitted during the absorption correction.
;
# end Validation Reply Form

_audit_creation_date             2021-06-22
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 Cl5 I, C12 H8 N2'
_chemical_formula_sum            'C18 H8 Cl5 I N2'
_chemical_formula_weight         556.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18  H8  Br1  Cl5  N2  '
_chemical_oxdiff_usercomment     'C6Cl5I + BPA'
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'
Cl Cl 0.3639 0.7018 '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'
N N 0.0311 0.0180 '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                   3.95160(10)
_cell_length_b                   11.1045(2)
_cell_length_c                   12.2703(3)
_cell_angle_alpha                112.085(2)
_cell_angle_beta                 91.110(2)
_cell_angle_gamma                96.392(2)
_cell_volume                     494.72(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9836
_cell_measurement_temperature    290.00(10)
_cell_measurement_theta_max      76.7960
_cell_measurement_theta_min      3.8670
_shelx_estimated_absorpt_T_max   0.533
_shelx_estimated_absorpt_T_min   0.167
_exptl_absorpt_coefficient_mu    18.974
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.439
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.868
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             268
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -7 1 0.0213
-1 0 7 0.0629
0 6 0 0.0112
0 7 -2 0.0177
-2 2 -6 0.0544
-2 -2 4 0.0628
1 -2 7 0.0582
2 0 1 0.0481
1 2 -7 0.0618
0 7 -4 0.0285
-2 6 -3 0.0394
1 3 4 0.0308

_exptl_crystal_size_max          0.147
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.038
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.3042 -6.8688 1.4771 -0.0245 -0.9668 0.2544
-0.9300 0.1820 6.9642 0.0107 0.3782 0.9257
0.0362 6.4373 0.4743 0.0256 0.9996 0.0090
0.3580 6.8982 -1.8752 0.0240 0.9512 -0.3076
-1.5887 1.7183 -6.0647 -0.8754 -0.1623 -0.4553
-2.2092 -1.5461 4.0311 -0.5922 -0.1110 0.7981
0.9926 -2.1638 7.2419 0.7201 0.1332 0.6809
2.4799 -0.1105 1.3218 0.9580 0.1784 -0.2246
1.1833 2.3957 -7.1239 0.0682 0.0138 -0.9976
-0.4238 7.1545 -3.7448 -0.3504 0.8458 -0.4022
-1.6223 6.0452 -2.6047 -0.7232 0.6853 -0.0858
1.1156 3.2679 3.8932 0.5890 0.7681 0.2513

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10654
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.251
_diffrn_reflns_theta_min         4.332
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00 -35.00   0.50    0.23    --  -47.91 -45.00 155.00  168
  2  ω     35.00 120.00   0.50    0.23    --   47.91  45.00 -54.00  170
  3  ω    -24.00  53.00   0.50    0.23    --   47.91 -45.00 155.00  154
  4  ω   -163.00 -79.00   0.50    0.92    --  -91.75 -45.00 155.00  168
  5  ω    -49.00 -20.00   0.50    0.92    --  -91.75  45.00 -54.00   58
  6  ω     95.00 178.00   0.50    0.92    --  107.78  45.00 -54.00  166
  7  ω   -119.00 -73.00   0.50    0.23    --  -47.91-125.00  90.00   92
  8  ω   -119.00 -73.00   0.50    0.23    --  -47.91-125.00 -90.00   92
  9  ω    -49.00  24.00   0.50    0.23    --  -47.91  45.00 -54.00  146
 10  ω    -24.00  28.00   0.50    0.23    --  -47.91  19.00-180.00  104
 11  ω     34.00  96.00   0.50    0.23    --   47.91-125.00-180.00  124
 12  ω   -166.00 -79.00   0.50    0.92    --  -91.75 -19.00-150.00  174
 13  ω    -85.00 -19.00   0.50    0.92    --  -91.75 125.00 -30.00  132
 14  ω    -64.00 -19.00   0.50    0.92    --  -91.75  57.00 120.00   90
 15  ω   -103.00 -19.00   0.50    0.92    --  -91.75  77.00  60.00  168
 16  ω     35.00 107.00   0.50    0.92    --  107.78 -77.00 120.00  144
 17  ω     35.00  68.00   0.50    0.92    --  107.78 -57.00 -60.00   66
 18  ω     95.00 178.00   0.50    0.92    --  107.78  19.00  90.00  166
 19  ω     35.00 106.00   0.50    0.92    --  107.78 -99.00 120.00  142
 20  ω     35.00 106.00   0.50    0.92    --  107.78 -99.00-150.00  142
 21  ω     93.00 178.00   0.50    0.92    --  107.78  57.00   0.00  170
 22  ω     35.00 106.00   0.50    0.92    --  107.78 -99.00  90.00  142
 23  ω     35.00 112.00   0.50    0.92    --  107.78-125.00 120.00  154
 24  ω     35.00  68.00   0.50    0.92    --  107.78 -57.00 120.00   66
 25  ω     35.00 106.00   0.50    0.92    --  107.78 -99.00 -90.00  142
 26  ω     35.00 106.00   0.50    0.92    --  107.78 -99.00 -60.00  142
 27  ω   -121.00 -35.00   0.50    0.23    --  -47.91 -38.00-150.00  172
 28  ω   -119.00 -73.00   0.50    0.23    --  -47.91-125.00   0.00   92
 29  ω   -119.00 -25.00   0.50    0.23    --  -47.91 -77.00 -90.00  188
 30  ω     25.00 121.00   0.50    0.23    --   47.91  77.00-120.00  192
 31  ω     25.00 121.00   0.50    0.23    --   47.91  77.00  30.00  192
 32  ω     25.00 121.00   0.50    0.23    --   47.91  77.00  90.00  192
 33  ω     33.00 120.00   0.50    0.23    --   47.91  57.00  30.00  174
 34  ω     25.00 121.00   0.50    0.23    --   47.91  77.00 150.00  192
 35  ω     25.00 121.00   0.50    0.23    --   47.91  77.00 -30.00  192
 36  ω   -163.00-103.00   0.50    0.92    --  -91.75 -77.00 150.00  120
 37  ω   -163.00 -77.00   0.50    0.92    --  -91.75 -57.00   0.00  172
 38  ω   -163.00 -69.00   0.50    0.92    --  -91.75 -77.00  60.00  188
 39  ω   -163.00 -69.00   0.50    0.92    --  -91.75 -77.00-150.00  188
 40  ω   -163.00 -69.00   0.50    0.92    --  -91.75 -77.00-120.00  188
 41  ω   -163.00 -69.00   0.50    0.92    --  -91.75 -77.00 120.00  188
 42  ω   -163.00 -69.00   0.50    0.92    --  -91.75 -77.00   0.00  188
 43  ω   -163.00 -69.00   0.50    0.92    --  -91.75 -77.00 -60.00  188
 44  ω   -163.00 -69.00   0.50    0.92    --  -91.75 -77.00  90.00  188
 45  ω   -163.00 -69.00   0.50    0.92    --  -91.75 -77.00 -90.00  188
 46  ω   -163.00 -69.00   0.50    0.92    --  -91.75 -77.00 -30.00  188
 47  ω   -163.00 -77.00   0.50    0.92    --  -91.75 -57.00 150.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.3597748000
_diffrn_orient_matrix_UB_12      -0.0016977000
_diffrn_orient_matrix_UB_13      0.0496193000
_diffrn_orient_matrix_UB_21      0.0483588000
_diffrn_orient_matrix_UB_22      0.1508292000
_diffrn_orient_matrix_UB_23      0.0568238000
_diffrn_orient_matrix_UB_31      -0.1510000000
_diffrn_orient_matrix_UB_32      -0.0060650000
_diffrn_orient_matrix_UB_33      0.1129112000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1837
_reflns_number_total             1944
_reflns_odcompleteness_completeness 99.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1944
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0252
_refine_ls_restrained_S_all      1.075
_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)+(0.0318P)²+0.1460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0633
_refine_ls_wR_factor_ref         0.0643
_refine_special_details          
'The C6Cl5I sits on an inversion site, which results in the atoms I1 and Cl1 occupying the same crystallographic space. The site occupancies for these two atoms were constrained to 0.5.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: I1(0.5) Cl1(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8)
;
_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 1.1958(6) 0.71507(18) 0.79070(17) 0.0435(2) Uani 0.5 1 d . . P A 2
Cl1 Cl 1.212(2) 0.7349(7) 0.8098(7) 0.0514(13) Uani 0.5 1 d . . P A 1
Cl2 Cl 1.28099(18) 1.00172(7) 0.76552(5) 0.05802(19) Uani 1 1 d . . . . .
Cl3 Cl 1.0953(2) 1.25782(7) 0.95260(6) 0.0624(2) Uani 1 1 d . . . . .
C1 C 1.0846(6) 0.8831(2) 0.9146(2) 0.0425(5) Uani 1 1 d . . . . .
C2 C 1.1254(6) 1.0000(2) 0.8951(2) 0.0419(5) Uani 1 1 d . . . . .
C3 C 1.0416(6) 1.1152(2) 0.9796(2) 0.0430(5) Uani 1 1 d . . . . .
N1 N 0.6434(7) 0.5417(2) 0.3575(2) 0.0604(6) Uani 1 1 d . . . . .
C4 C 0.7331(7) 0.6222(2) 0.4679(3) 0.0544(6) Uani 1 1 d . . . . .
H4 H 0.826457 0.587902 0.518338 0.065 Uiso 1 1 calc R U . . .
C5 C 0.6966(7) 0.7538(2) 0.5123(2) 0.0469(5) Uani 1 1 d . . . . .
H5 H 0.763564 0.806009 0.590527 0.056 Uiso 1 1 calc R U . . .
C6 C 0.5586(6) 0.8066(2) 0.4386(2) 0.0415(5) Uani 1 1 d . . . . .
C7 C 0.4602(8) 0.7235(3) 0.3232(2) 0.0539(6) Uani 1 1 d . . . . .
H7 H 0.363896 0.754646 0.270798 0.065 Uiso 1 1 calc R U . . .
C8 C 0.5088(9) 0.5936(3) 0.2882(3) 0.0632(8) Uani 1 1 d . . . . .
H8 H 0.442641 0.538626 0.210615 0.076 Uiso 1 1 calc R U . . .
C9 C 0.5169(6) 0.9435(2) 0.4815(2) 0.0446(5) 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 2.015(3) . ?
Cl1 C1 1.799(8) . ?
Cl2 C2 1.722(2) . ?
Cl3 C3 1.727(3) . ?
C1 C2 1.398(4) . ?
C1 C3 1.395(3) 2_777 ?
C2 C3 1.390(3) . ?
N1 C4 1.326(4) . ?
N1 C8 1.326(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(4) . ?
C6 C7 1.387(4) . ?
C6 C9 1.440(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.379(4) . ?
C8 H8 0.9300 . ?
C9 C9 1.187(5) 2_676 ?

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 I1 120.65(19) . . ?
C2 C1 Cl1 121.3(3) . . ?
C3 C1 I1 120.70(19) 2_777 . ?
C3 C1 Cl1 120.0(3) 2_777 . ?
C3 C1 C2 118.6(2) 2_777 . ?
C1 C2 Cl2 119.91(18) . . ?
C3 C2 Cl2 119.51(19) . . ?
C3 C2 C1 120.6(2) . . ?
C1 C3 Cl3 119.86(19) 2_777 . ?
C2 C3 Cl3 119.35(18) . . ?
C2 C3 C1 120.8(2) . 2_777 ?
C8 N1 C4 116.4(2) . . ?
N1 C4 H4 118.0 . . ?
N1 C4 C5 124.0(3) . . ?
C5 C4 H4 118.0 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.9(2) . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C7 117.9(2) . . ?
C5 C6 C9 120.6(2) . . ?
C7 C6 C9 121.5(2) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 C6 118.3(3) . . ?
C8 C7 H7 120.8 . . ?
N1 C8 C7 124.5(3) . . ?
N1 C8 H8 117.8 . . ?
C7 C8 H8 117.8 . . ?
C9 C9 C6 179.1(4) 2_676 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C1 C2 Cl2 -1.5(3) . . . . ?
I1 C1 C2 C3 178.59(18) . . . . ?
Cl1 C1 C2 Cl2 3.2(4) . . . . ?
Cl1 C1 C2 C3 -176.8(4) . . . . ?
Cl2 C2 C3 Cl3 0.0(3) . . . . ?
Cl2 C2 C3 C1 -179.92(17) . . . 2_777 ?
C1 C2 C3 Cl3 179.97(17) . . . . ?
C1 C2 C3 C1 0.0(4) . . . 2_777 ?
C3 C1 C2 Cl2 179.92(17) 2_777 . . . ?
C3 C1 C2 C3 0.0(4) 2_777 . . . ?
N1 C4 C5 C6 -0.1(4) . . . . ?
C4 N1 C8 C7 0.4(5) . . . . ?
C4 C5 C6 C7 0.7(4) . . . . ?
C4 C5 C6 C9 -179.9(2) . . . . ?
C5 C6 C7 C8 -0.7(4) . . . . ?
C6 C7 C8 N1 0.2(5) . . . . ?
C8 N1 C4 C5 -0.5(4) . . . . ?
C9 C6 C7 C8 179.8(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen 75 micron MicroLoop'
_olex2_submission_original_sample_id gro21_19
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   923
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.429
_oxdiff_exptl_absorpt_empirical_full_min 0.749
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
####################################################################### 
# 
# 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_C6ICl5_AP
_database_code_depnum_ccdc_archive 'CCDC 2106692'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2021-08-31 deposited with the CCDC.	2021-11-22 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT336_C6ICl5_AP           
;
PROBLEM: Long Bond Distance for ..... C1       -Cl1            1.859 Ang.  
RESPONSE: Due to the overlap of Cl1 and I1 on the same crystallographic 
          position.
;
_vrf_PLAT911_C6ICl5_AP           
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         20 Report
RESPONSE: These reflections were omitted during the absorption correction.
;
# end Validation Reply Form


_audit_creation_date             2021-06-23
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 Cl5 I, C10 H8 N4'
_chemical_formula_sum            'C16 H8 Cl5 I N4'
_chemical_formula_weight         560.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16  H8  I1  Cl5  N4  '
_chemical_oxdiff_usercomment     'C6Cl5I + Azo'
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'
Cl Cl 0.3639 0.7018 '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'
N N 0.0311 0.0180 '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                   3.91440(10)
_cell_length_b                   10.69090(10)
_cell_length_c                   12.4925(2)
_cell_angle_alpha                111.5100(10)
_cell_angle_beta                 93.2050(10)
_cell_angle_gamma                91.8070(10)
_cell_volume                     484.858(16)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9834
_cell_measurement_temperature    290.00(10)
_cell_measurement_theta_max      76.8540
_cell_measurement_theta_min      3.7840
_shelx_estimated_absorpt_T_max   0.526
_shelx_estimated_absorpt_T_min   0.119
_exptl_absorpt_coefficient_mu    19.394
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_correction_T_min  0.189
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.919
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             270
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 2 0.0151
-2 3 -3 0.0535
0 4 -8 0.0169
0 6 0 0.0581
2 4 -1 0.0489
0 -6 -1 0.0649
-1 5 2 0.0662
-2 -1 -5 0.0519

_exptl_crystal_size_max          0.191
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.038
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 -0.9988 1.9982 0.2508 0.0021 0.0351
-2.1563 3.4324 -2.8686 -0.5869 0.0159 0.8095
-0.0701 4.1842 -7.7906 -0.9945 0.0254 -0.1014
0.3975 6.1649 0.4210 -0.1822 0.9805 0.0734
2.0801 3.7181 -1.1574 -0.1345 0.7197 -0.6811
-0.0526 -6.1953 -0.6891 0.1785 -0.9612 -0.2105
-1.2454 5.1978 1.5670 -0.1325 0.7165 0.6849
-1.6849 -1.1327 -4.6077 -0.5504 -0.7189 0.4245

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10832
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.039
_diffrn_reflns_theta_min         3.813
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     26.00 121.00   0.50    0.11    --   48.16  77.00  90.00  190
  2  ω     26.00 121.00   0.50    0.11    --   48.16  77.00  30.00  190
  3  ω     26.00 121.00   0.50    0.11    --   48.16  77.00-180.00  190
  4  ω    -64.00 -19.00   0.50    0.44    --  -91.75  57.00-180.00   90
  5  ω    -24.00  27.00   0.50    0.11    --  -48.16  19.00-180.00  102
  6  ω    -24.00  27.00   0.50    0.11    --  -48.16  19.00-120.00  102
  7  ω    -24.00  27.00   0.50    0.11    --  -48.16  19.00 -60.00  102
  8  ω    -24.00  27.00   0.50    0.11    --  -48.16  19.00 -30.00  102
  9  ω     35.00 106.00   0.50    0.44    --  107.78 -99.00  90.00  142
 10  ω     35.00 107.00   0.50    0.44    --  107.78-105.00 165.00  144
 11  ω     18.00  85.00   0.50    0.11    --   48.16-105.00 165.00  134
 12  ω     35.00 106.00   0.50    0.44    --  107.78 -99.00  30.00  142
 13  ω     35.00 106.00   0.50    0.44    --  107.78 -99.00   0.00  142
 14  ω     35.00  68.00   0.50    0.44    --  107.78 -57.00-180.00   66
 15  ω     35.00 107.00   0.50    0.44    --  107.78 -77.00 -60.00  144
 16  ω     35.00  68.00   0.50    0.44    --  107.78 -57.00   0.00   66
 17  ω     35.00  68.00   0.50    0.44    --  107.78 -57.00  30.00   66
 18  ω     35.00  68.00   0.50    0.44    --  107.78 -57.00  90.00   66
 19  ω     35.00 107.00   0.50    0.44    --  107.78 -77.00 150.00  144
 20  ω    105.00 178.00   0.50    0.44    --  107.78 105.00 -95.00  146
 21  ω     93.00 178.00   0.50    0.44    --  107.78  57.00-120.00  170
 22  ω     95.00 178.00   0.50    0.44    --  107.78  38.00-180.00  166
 23  ω     95.00 178.00   0.50    0.44    --  107.78  38.00-150.00  166
 24  ω    -85.00 -19.00   0.50    0.44    --  -91.75 125.00-150.00  132
 25  ω    -85.00 -19.00   0.50    0.44    --  -91.75 125.00 -90.00  132
 26  ω    -81.00 -19.00   0.50    0.44    --  -91.75 105.00 -95.00  124
 27  ω    -81.00   3.00   0.50    0.11    --  -48.16 105.00 -95.00  168
 28  ω   -121.00 -25.00   0.50    0.11    --  -48.16 -77.00 -60.00  192
 29  ω   -120.00 -33.00   0.50    0.11    --  -48.16 -57.00   0.00  174
 30  ω   -120.00 -33.00   0.50    0.11    --  -48.16 -57.00-120.00  174
 31  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00-180.00  188
 32  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00-150.00  188
 33  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00-120.00  188
 34  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00 -60.00  188
 35  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00 -30.00  188
 36  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00  30.00  188
 37  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00  60.00  188
 38  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00 120.00  188
 39  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00 150.00  188
 40  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00  90.00  188
 41  ω   -166.00 -79.00   0.50    0.44    --  -91.75 -19.00   0.00  174
 42  ω   -166.00 -79.00   0.50    0.44    --  -91.75 -19.00 -60.00  174
 43  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00 -90.00  188
 44  ω   -121.00 -73.00   0.50    0.11    --  -48.16-125.00-150.00   96
 45  ω   -121.00 -73.00   0.50    0.11    --  -48.16-125.00 -90.00   96
 46  ω   -163.00 -73.00   0.50    0.44    --  -91.75-125.00 -30.00  180
 47  ω   -163.00 -83.00   0.50    0.44    --  -91.75-105.00 165.00  160
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0671301000
_diffrn_orient_matrix_UB_12      -0.0410580000
_diffrn_orient_matrix_UB_13      0.1050012000
_diffrn_orient_matrix_UB_21      0.1264250000
_diffrn_orient_matrix_UB_22      0.1458462000
_diffrn_orient_matrix_UB_23      0.0739376000
_diffrn_orient_matrix_UB_31      -0.3679352000
_diffrn_orient_matrix_UB_32      0.0332975000
_diffrn_orient_matrix_UB_33      0.0342152000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1830
_reflns_number_total             1902
_reflns_odcompleteness_completeness 98.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.0049(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1902
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0272
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0449P)²+0.1162P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0758
_refine_special_details          
'The C6Cl5I sits on an inversion site, which results in the atoms I1 and Cl1 occupying the same crystallographic space. The site occupancies for these two atoms were constrained to 0.5. The azo moiety was also positionally disordered over two sites (A and B). The site occupancies for the A and B sites refined to 0.94 and 0.06, respectively.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 N2A, N2B, C7, C6, C8, N1, C4, C5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Others
 Sof(N2B)=1-FVAR(1)
 Sof(N2A)=FVAR(1)
 Fixed Sof: I1(0.5) Cl1(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8)
;
_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 1.2015(2) 0.71801(10) 0.78590(9) 0.04324(19) Uani 0.5 1 d . . P A 2
Cl1 Cl 1.1953(16) 0.7240(6) 0.7952(5) 0.091(3) Uani 0.5 1 d . . P A 1
Cl2 Cl 1.2738(2) 1.01490(8) 0.77553(5) 0.0602(2) Uani 1 1 d . . . . .
Cl3 Cl 1.0893(2) 1.27620(8) 0.96969(7) 0.0668(3) Uani 1 1 d . . . . .
C1 C 1.0844(7) 0.8816(3) 0.9114(2) 0.0458(6) Uani 1 1 d . . . . .
C2 C 1.1206(7) 1.0060(3) 0.8997(2) 0.0454(6) Uani 1 1 d . . . . .
C3 C 1.0376(7) 1.1234(3) 0.9872(2) 0.0474(6) Uani 1 1 d . . . . .
N1 N 0.6105(8) 0.5500(2) 0.3688(2) 0.0591(6) Uani 1 1 d . . . . .
C4 C 0.7127(9) 0.6376(3) 0.4737(3) 0.0557(7) Uani 1 1 d . . . . .
H4 H 0.816792 0.604834 0.526176 0.067 Uiso 1 1 calc R U . . .
C5 C 0.6724(8) 0.7751(3) 0.5091(2) 0.0496(6) Uani 1 1 d . . . . .
H5 H 0.747903 0.833232 0.583170 0.060 Uiso 1 1 calc R U . . .
C6 C 0.5163(7) 0.8230(2) 0.4308(2) 0.0450(5) Uani 1 1 d . . . . .
C7 C 0.4045(9) 0.7336(3) 0.3225(2) 0.0546(6) Uani 1 1 d . . . . .
H7 H 0.295958 0.762933 0.268500 0.066 Uiso 1 1 calc R U . . .
C8 C 0.4585(9) 0.5988(3) 0.2964(3) 0.0595(7) Uani 1 1 d . . . . .
H8 H 0.383199 0.538476 0.223165 0.071 Uiso 1 1 calc R U . . .
N2A N 0.4573(7) 0.9617(3) 0.4508(2) 0.0480(8) Uani 0.937(8) 1 d . . P B 1
N2B N 0.529(12) 0.964(5) 0.527(4) 0.055(9) Uani 0.063(8) 1 d . . P B 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 1.961(3) . ?
Cl1 C1 1.859(7) . ?
Cl2 C2 1.728(2) . ?
Cl3 C3 1.733(3) . ?
C1 C2 1.393(4) . ?
C1 C3 1.397(4) 2_777 ?
C2 C3 1.391(4) . ?
N1 C4 1.331(4) . ?
N1 C8 1.323(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(4) . ?
C6 C7 1.377(4) . ?
C6 N2A 1.439(4) . ?
C6 N2B 1.54(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(4) . ?
C8 H8 0.9300 . ?
N2A N2A 1.222(6) 2_676 ?
N2B N2B 1.22(10) 2_676 ?

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 I1 119.78(19) . . ?
C2 C1 Cl1 121.3(3) . . ?
C2 C1 C3 118.8(2) . 2_777 ?
C3 C1 I1 121.4(2) 2_777 . ?
C3 C1 Cl1 119.9(3) 2_777 . ?
C1 C2 Cl2 119.7(2) . . ?
C3 C2 Cl2 119.5(2) . . ?
C3 C2 C1 120.9(2) . . ?
C1 C3 Cl3 120.2(2) 2_777 . ?
C2 C3 Cl3 119.4(2) . . ?
C2 C3 C1 120.3(3) . 2_777 ?
C8 N1 C4 117.0(2) . . ?
N1 C4 H4 118.2 . . ?
N1 C4 C5 123.6(3) . . ?
C5 C4 H4 118.2 . . ?
C4 C5 H5 121.1 . . ?
C6 C5 C4 117.9(3) . . ?
C6 C5 H5 121.1 . . ?
C5 C6 N2A 125.9(2) . . ?
C5 C6 N2B 88.6(19) . . ?
C7 C6 C5 119.3(2) . . ?
C7 C6 N2A 114.8(2) . . ?
C7 C6 N2B 151.5(19) . . ?
C6 C7 H7 121.0 . . ?
C6 C7 C8 117.9(3) . . ?
C8 C7 H7 121.0 . . ?
N1 C8 C7 124.3(3) . . ?
N1 C8 H8 117.9 . . ?
C7 C8 H8 117.9 . . ?
N2A N2A C6 113.6(3) 2_676 . ?
N2B N2B C6 102(5) 2_676 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C1 C2 Cl2 -0.8(3) . . . . ?
I1 C1 C2 C3 179.66(19) . . . . ?
Cl1 C1 C2 Cl2 -0.4(4) . . . . ?
Cl1 C1 C2 C3 -179.9(3) . . . . ?
Cl2 C2 C3 Cl3 0.1(3) . . . . ?
Cl2 C2 C3 C1 -179.5(2) . . . 2_777 ?
C1 C2 C3 Cl3 179.5(2) . . . . ?
C1 C2 C3 C1 -0.1(4) . . . 2_777 ?
C3 C1 C2 Cl2 179.54(19) 2_777 . . . ?
C3 C1 C2 C3 0.1(4) 2_777 . . . ?
N1 C4 C5 C6 0.2(5) . . . . ?
C4 N1 C8 C7 0.8(5) . . . . ?
C4 C5 C6 C7 0.7(4) . . . . ?
C4 C5 C6 N2A -178.9(3) . . . . ?
C4 C5 C6 N2B 174.6(17) . . . . ?
C5 C6 C7 C8 -0.9(4) . . . . ?
C5 C6 N2A N2A -3.9(5) . . . 2_676 ?
C5 C6 N2B N2B 165(5) . . . 2_676 ?
C6 C7 C8 N1 0.1(5) . . . . ?
C7 C6 N2A N2A 176.5(3) . . . 2_676 ?
C7 C6 N2B N2B -26(8) . . . 2_676 ?
C8 N1 C4 C5 -1.0(5) . . . . ?
N2A C6 C7 C8 178.8(3) . . . . ?
N2B C6 C7 C8 -168(4) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen 75 micron MicroLoop'
_olex2_submission_original_sample_id gro21_20
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.474
_oxdiff_exptl_absorpt_empirical_full_min 0.666

# END of CIF


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
####################################################################### 
# 
# 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_C6ICl5_BPE
_database_code_depnum_ccdc_archive 'CCDC 2106690'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2021-08-31 deposited with the CCDC.	2021-11-22 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT911_C6ICl5_BPE          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         14 Report
RESPONSE: These reflections were omitted during the absorption correction.
;
# end Validation Reply Form

_audit_creation_date             2021-06-22
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 Cl5 I, C12 H10 N2'
_chemical_formula_sum            'C18 H10 Cl5 I N2'
_chemical_formula_weight         558.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18  H10  I1  Cl5  N2  '
_chemical_oxdiff_usercomment     'C6Cl5I + BPE'
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'
Cl Cl 0.3639 0.7018 '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'
N N 0.0311 0.0180 '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                   3.97460(10)
_cell_length_b                   10.7984(2)
_cell_length_c                   12.4426(3)
_cell_angle_alpha                111.056(2)
_cell_angle_beta                 93.327(2)
_cell_angle_gamma                93.491(2)
_cell_volume                     495.61(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9040
_cell_measurement_temperature    290.00(10)
_cell_measurement_theta_max      77.1690
_cell_measurement_theta_min      3.7930
_shelx_estimated_absorpt_T_max   0.368
_shelx_estimated_absorpt_T_min   0.180
_exptl_absorpt_coefficient_mu    18.940
_exptl_absorpt_correction_T_max  0.661
_exptl_absorpt_correction_T_min  0.236
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.871
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             270
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 2 -1 0.0379
-1 7 -4 0.0348
2 0 3 0.0594
-1 -7 2 0.0169
1 0 -8 0.0617
2 -2 -1 0.0692
2 -2 6 0.0622
0 -1 8 0.0427
-2 2 2 0.0463
2 0 5 0.0529
0 4 4 0.0360
-1 5 1 0.0285
-2 3 -4 0.0676
2 2 -4 0.0528
0 4 -8 0.0441
2 3 -2 0.0576

_exptl_crystal_size_max          0.138
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.066
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0006 1.9998 -1.0039 -0.2632 0.0476 -0.1032
-0.6642 6.7742 -3.8958 -0.7941 0.1047 -0.5986
2.2664 0.3038 2.8167 -0.4139 0.0533 0.9088
-0.5092 -6.7514 2.3570 0.9844 -0.1292 0.1194
0.6378 0.3158 -7.5551 0.1261 0.9597 -0.2513
2.4301 -2.2752 -1.1782 0.0808 0.6232 0.7778
1.7491 -2.4498 5.5984 -0.0351 -0.2597 0.9651
-0.2508 -0.7324 7.7980 -0.1194 -0.9077 0.4022
-2.3478 2.0548 2.2755 -0.0946 -0.7271 -0.6800
1.6250 0.1551 5.3418 -0.3976 -0.3387 0.8528
-0.0289 4.1055 4.3683 -0.7497 -0.6409 0.1649
-1.4385 5.3043 1.1832 -0.6505 -0.5570 -0.5164
-2.0628 3.2286 -4.1135 -0.0914 0.0109 -0.9958
2.1695 2.1758 -4.4766 -0.4378 0.8062 0.3980
-0.0911 4.4047 -7.6669 -0.3876 0.7117 -0.5859
2.3276 2.5894 -2.2178 -0.5932 0.5615 0.5769

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11021
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.065
_diffrn_reflns_theta_min         3.821
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     26.00 121.00   0.50    0.11    --   48.16  77.00-120.00  190
  2  ω     95.00 178.00   0.50    0.44    --  107.78  38.00-120.00  166
  3  ω     95.00 178.00   0.50    0.44    --  107.78  38.00 -90.00  166
  4  ω     26.00 121.00   0.50    0.11    --   48.16  77.00  60.00  190
  5  ω    101.00 178.00   0.50    0.44    --  107.78  86.00 131.00  154
  6  ω    -21.00  75.00   0.50    0.11    --   48.16 -86.00  13.00  192
  7  ω     35.00 112.00   0.50    0.44    --  107.78-125.00-120.00  154
  8  ω     35.00 106.00   0.50    0.44    --  107.78 -99.00 -60.00  142
  9  ω     35.00 106.00   0.50    0.44    --  107.78 -99.00   0.00  142
 10  ω     35.00 106.00   0.50    0.44    --  107.78 -99.00  30.00  142
 11  ω     35.00 106.00   0.50    0.44    --  107.78 -99.00 150.00  142
 12  ω     35.00 135.00   0.50    0.44    --  107.78 -86.00  13.00  200
 13  ω     35.00 107.00   0.50    0.44    --  107.78 -77.00 -90.00  144
 14  ω     35.00 107.00   0.50    0.44    --  107.78 -77.00-150.00  144
 15  ω     35.00  68.00   0.50    0.44    --  107.78 -57.00  60.00   66
 16  ω     35.00  68.00   0.50    0.44    --  107.78 -57.00  90.00   66
 17  ω     35.00  68.00   0.50    0.44    --  107.78 -57.00 150.00   66
 18  ω    -25.00  45.00   0.50    0.11    --   48.16 -38.00 120.00  140
 19  ω    -41.00  25.00   0.50    0.11    --  -48.16  38.00  30.00  132
 20  ω    -64.00 -19.00   0.50    0.44    --  -91.75  57.00 -60.00   90
 21  ω    -64.00 -19.00   0.50    0.44    --  -91.75  57.00 -30.00   90
 22  ω    -64.00 -19.00   0.50    0.44    --  -91.75  57.00   0.00   90
 23  ω    -64.00 -19.00   0.50    0.44    --  -91.75  57.00  60.00   90
 24  ω    -75.00  25.00   0.50    0.11    --  -48.16  86.00 131.00  200
 25  ω    -75.00  25.00   0.50    0.11    --  -48.16  86.00 131.00  200
 26  ω   -118.00 -19.00   0.50    0.44    --  -91.75  86.00 131.00  198
 27  ω   -121.00 -25.00   0.50    0.11    --  -48.16 -77.00 150.00  192
 28  ω   -121.00 -25.00   0.50    0.11    --  -48.16 -77.00  60.00  192
 29  ω   -121.00 -35.00   0.50    0.11    --  -48.16 -38.00 150.00  172
 30  ω   -120.00 -33.00   0.50    0.11    --  -48.16 -57.00 -30.00  174
 31  ω   -121.00 -25.00   0.50    0.11    --  -48.16 -77.00 -60.00  192
 32  ω   -120.00 -33.00   0.50    0.11    --  -48.16 -57.00-120.00  174
 33  ω   -163.00 -95.00   0.50    0.44    --  -91.75 -77.00-150.00  136
 34  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00 -90.00  188
 35  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00 -60.00  188
 36  ω   -163.00 -71.00   0.50    0.44    --  -91.75 -71.00 -29.55  184
 37  ω   -163.00 -70.00   0.50    0.44    --  -91.75 -74.00  18.60  186
 38  ω   -163.00 -74.00   0.50    0.44    --  -91.75 -63.00  55.76  178
 39  ω   -163.00 -74.00   0.50    0.44    --  -91.75 -63.00 150.58  178
 40  ω   -165.00 -78.00   0.50    0.44    --  -91.75 -38.00 150.00  174
 41  ω   -163.00 -77.00   0.50    0.44    --  -91.75 -57.00 120.00  172
 42  ω   -163.00 -77.00   0.50    0.44    --  -91.75 -57.00  90.00  172
 43  ω   -163.00 -69.00   0.50    0.44    --  -91.75 -77.00  60.00  188
 44  ω   -163.00 -77.00   0.50    0.44    --  -91.75 -57.00-150.00  172
 45  ω   -121.00 -73.00   0.50    0.11    --  -48.16-125.00-180.00   96
 46  ω   -163.00 -79.00   0.50    0.44    --  -91.75 -86.00  13.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1215638000
_diffrn_orient_matrix_UB_12      -0.1482098000
_diffrn_orient_matrix_UB_13      -0.0331434000
_diffrn_orient_matrix_UB_21      0.1697837000
_diffrn_orient_matrix_UB_22      -0.0335060000
_diffrn_orient_matrix_UB_23      -0.1140904000
_diffrn_orient_matrix_UB_31      0.3291054000
_diffrn_orient_matrix_UB_32      -0.0215147000
_diffrn_orient_matrix_UB_33      0.0601453000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1836
_reflns_number_total             1952
_reflns_odcompleteness_completeness 99.32
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.0037(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1952
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0281
_refine_ls_restrained_S_all      1.056
_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)+(0.0403P)²+0.1238P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0740
_refine_special_details          
'The C6Cl5I sits on an inversion site, which results in the atoms I1 and Cl1 occupying the same crystallographic space. The site occupancies for these two atoms were constrained to 0.5.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: I1(0.5) Cl1(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C9(H9)
;
_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 1.1855(6) 0.7187(2) 0.7854(2) 0.0456(3) Uani 0.5 1 d . . P A 2
Cl1 Cl 1.195(3) 0.7356(9) 0.8044(8) 0.0540(16) Uani 0.5 1 d . . P A 1
Cl2 Cl 1.2695(2) 1.01567(9) 0.77501(6) 0.0636(2) Uani 1 1 d . . . . .
Cl3 Cl 1.1002(2) 1.27224(9) 0.96738(7) 0.0698(2) Uani 1 1 d . . . . .
C1 C 1.0780(7) 0.8836(3) 0.9119(2) 0.0468(6) Uani 1 1 d . . . . .
C2 C 1.1205(7) 1.0064(3) 0.8996(2) 0.0476(6) Uani 1 1 d . . . . .
C3 C 1.0421(7) 1.1222(3) 0.9862(2) 0.0478(6) Uani 1 1 d . . . . .
N1 N 0.6393(7) 0.5406(2) 0.3621(2) 0.0584(6) Uani 1 1 d . . . . .
C4 C 0.7294(8) 0.6292(3) 0.4680(3) 0.0542(7) Uani 1 1 d . . . . .
H4 H 0.840235 0.599756 0.520988 0.065 Uiso 1 1 calc R U . . .
C5 C 0.6687(7) 0.7618(3) 0.5040(2) 0.0469(6) Uani 1 1 d . . . . .
H5 H 0.737967 0.819199 0.579036 0.056 Uiso 1 1 calc R U . . .
C6 C 0.5021(7) 0.8088(2) 0.4264(2) 0.0406(5) Uani 1 1 d . . . . .
C7 C 0.4044(8) 0.7165(3) 0.3168(3) 0.0524(7) Uani 1 1 d . . . . .
H7 H 0.289726 0.742267 0.262063 0.063 Uiso 1 1 calc R U . . .
C8 C 0.4782(9) 0.5862(3) 0.2895(3) 0.0614(8) Uani 1 1 d . . . . .
H8 H 0.410485 0.526250 0.215245 0.074 Uiso 1 1 calc R U . . .
C9 C 0.4275(7) 0.9483(2) 0.4559(2) 0.0416(5) Uani 1 1 d . . . . .
H9 H 0.262947 0.965481 0.408090 0.050 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 1.997(4) . ?
Cl1 C1 1.784(10) . ?
Cl2 C2 1.725(3) . ?
Cl3 C3 1.722(3) . ?
C1 C2 1.390(4) . ?
C1 C3 1.401(4) 2_777 ?
C2 C3 1.393(4) . ?
N1 C4 1.333(4) . ?
N1 C8 1.326(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.395(4) . ?
C6 C7 1.385(4) . ?
C6 C9 1.471(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.378(4) . ?
C8 H8 0.9300 . ?
C9 C9 1.323(5) 2_676 ?
C9 H9 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 I1 120.1(2) . . ?
C2 C1 Cl1 121.4(3) . . ?
C2 C1 C3 119.0(3) . 2_777 ?
C3 C1 I1 120.9(2) 2_777 . ?
C3 C1 Cl1 119.6(4) 2_777 . ?
C1 C2 Cl2 119.6(2) . . ?
C1 C2 C3 120.9(2) . . ?
C3 C2 Cl2 119.4(2) . . ?
C1 C3 Cl3 120.6(2) 2_777 . ?
C2 C3 Cl3 119.3(2) . . ?
C2 C3 C1 120.1(3) . 2_777 ?
C8 N1 C4 116.1(2) . . ?
N1 C4 H4 117.9 . . ?
N1 C4 C5 124.2(3) . . ?
C5 C4 H4 117.9 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.1(3) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C9 123.4(2) . . ?
C7 C6 C5 116.7(2) . . ?
C7 C6 C9 119.9(2) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.5(3) . . ?
C8 C7 H7 120.2 . . ?
N1 C8 C7 124.3(3) . . ?
N1 C8 H8 117.8 . . ?
C7 C8 H8 117.8 . . ?
C6 C9 H9 116.9 . . ?
C9 C9 C6 126.1(3) 2_676 . ?
C9 C9 H9 116.9 2_676 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C1 C2 Cl2 -0.5(3) . . . . ?
I1 C1 C2 C3 179.1(2) . . . . ?
Cl1 C1 C2 Cl2 3.2(5) . . . . ?
Cl1 C1 C2 C3 -177.2(4) . . . . ?
Cl2 C2 C3 Cl3 -0.7(3) . . . . ?
Cl2 C2 C3 C1 -179.8(2) . . . 2_777 ?
C1 C2 C3 Cl3 179.8(2) . . . . ?
C1 C2 C3 C1 0.7(5) . . . 2_777 ?
C3 C1 C2 Cl2 179.8(2) 2_777 . . . ?
C3 C1 C2 C3 -0.7(4) 2_777 . . . ?
N1 C4 C5 C6 0.2(5) . . . . ?
C4 N1 C8 C7 0.6(5) . . . . ?
C4 C5 C6 C7 0.7(4) . . . . ?
C4 C5 C6 C9 -179.6(3) . . . . ?
C5 C6 C7 C8 -0.9(4) . . . . ?
C5 C6 C9 C9 17.9(5) . . . 2_676 ?
C6 C7 C8 N1 0.2(5) . . . . ?
C7 C6 C9 C9 -162.3(3) . . . 2_676 ?
C8 N1 C4 C5 -0.8(5) . . . . ?
C9 C6 C7 C8 179.4(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen 75 micro MicroLoop'
_olex2_submission_original_sample_id gro21_18
_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 2.145
_oxdiff_exptl_absorpt_empirical_full_min 0.568
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
