# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

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

data_1_eb_a_156_2
_database_code_depnum_ccdc_archive 'CCDC 2264915'
loop_
_audit_author_name
_audit_author_address
'Eric Bosch'
;Missouri State University
United States of America
;
_audit_update_record             
;
2023-05-23 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_audit_creation_date             2023-04-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
loop_
_audit_author_email
?
_chemical_formula_moiety         'C12 H10 N2, 2(C6 H Cl4 I)'
_chemical_formula_sum            'C24 H12 Cl8 I2 N2'
_chemical_formula_weight         865.805
_chemical_oxdiff_formula         'C22 H12 Cl8 I2 N2'
_chemical_oxdiff_usercomment     'cut rod'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
I -0.19206 6.94430 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07120 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   4.0650(1)
_cell_length_b                   11.0283(2)
_cell_length_c                   32.1854(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.484(2)
_cell_angle_gamma                90
_cell_volume                     1442.39(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8144
_cell_measurement_temperature    299.36(13)
_cell_measurement_theta_max      78.6970
_cell_measurement_theta_min      2.7440
_exptl_absorpt_coefficient_mu    24.107
_exptl_absorpt_correction_T_max  0.543
_exptl_absorpt_correction_T_min  0.103
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.994
_exptl_crystal_description       block
_exptl_crystal_F_000             832.222
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -2 1 0.0329
-2 1 0 0.0468
0 -1 2 0.0238
0 1 -2 0.0075
0 -1 -2 0.0338
0 1 2 0.0285
1 0 -1 0.0556

_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
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
0.0002 -2.0006 0.9968 -0.0335 0.0669 0.2735
-2.0005 0.9972 0.0074 0.4399 -0.6299 0.0635
0.0002 -1.0007 1.9979 -0.0761 -0.0042 0.1513
-0.0002 1.0007 -1.9979 0.0761 0.0042 -0.1513
-0.0000 -0.9997 -2.0007 0.0821 0.0963 0.1125
0.0000 0.9997 2.0007 -0.0821 -0.0963 -0.1125
1.0002 0.0017 -1.0026 -0.1819 0.3171 -0.1074

_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.9988
_diffrn_reflns_Laue_measured_fraction_max 0.9926
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            14136
_diffrn_reflns_point_group_measured_fraction_full 0.9988
_diffrn_reflns_point_group_measured_fraction_max 0.9926
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         79.60
_diffrn_reflns_theta_min         4.24
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.36(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_measured_fraction_theta_max 0.9926
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     48.00  73.00   0.50    0.42    --  111.50-125.00 120.00   50
  2  ω     84.00 111.00   0.50    0.42    --  111.50-125.00 120.00   54
  3  ω     68.00  98.00   0.50    0.42    --  111.50-125.00  60.00   60
  4  ω     56.00 100.00   0.50    0.42    --  111.50 -95.00 120.00   88
  5  ω     40.00 104.00   0.50    0.42    --  111.50 -95.00 150.00  128
  6  ω     48.00  73.00   0.50    0.42    --  111.50 -95.00  90.00   50
  7  ω     55.00  81.00   0.50    0.42    --  111.50 -95.00 -90.00   52
  8  ω     75.00 105.00   0.50    0.42    --  111.50 -95.00-120.00   60
  9  ω     58.00  84.00   0.50    0.42    --  111.50 -95.00-150.00   52
 10  ω     43.00  71.00   0.50    0.42    --  111.50 -61.00-120.00   56
 11  ω     44.00  73.00   0.50    0.42    --  111.50 -61.00-180.00   58
 12  ω     43.00  75.00   0.50    0.42    --  111.50 -61.00 -30.00   64
 13  ω     42.00  76.00   0.50    0.42    --  111.50 -61.00  30.00   68
 14  ω     40.00  76.00   0.50    0.42    --  111.50 -61.00  90.00   72
 15  ω     57.00  84.00   0.50    0.42    --  111.50 -77.00 150.00   54
 16  ω     92.00 117.00   0.50    0.42    --  111.50 -80.00 150.34   50
 17  ω      5.00  33.00   0.50    0.11    --   48.90 -25.00-175.00   56
 18  ω    -22.00  48.00   0.50    0.11    --   48.90 -38.00  60.00  140
 19  ω    131.00 171.00   0.50    0.42    --  111.50 125.00-180.00   80
 20  ω    118.00 149.00   0.50    0.42    --  111.50 125.00 -60.00   62
 21  ω    117.00 172.00   0.50    0.42    --  111.50  77.00 -90.00  110
 22  ω    101.00 175.00   0.50    0.42    --  111.50  45.00-150.00  148
 23  ω    112.00 137.00   0.50    0.42    --  111.50  77.00-180.00   50
 24  ω    112.00 159.00   0.50    0.42    --  111.50  45.00-120.00   94
 25  ω    144.00 169.00   0.50    0.42    --  111.50  77.00-120.00   50
 26  ω    114.00 140.00   0.50    0.42    --  111.50  77.00-120.00   52
 27  ω    118.00 143.00   0.50    0.42    --  111.50  61.00 -60.00   50
 28  ω     43.00  93.00   0.50    0.11    --   48.90  25.00 -11.00  100
 29  ω    109.00 161.00   0.50    0.42    --  111.50  30.00 -60.00  104
 30  ω    101.00 163.00   0.50    0.42    --  111.50  30.00 -30.00  124
 31  ω    116.00 152.00   0.50    0.42    --  111.50  45.00   0.00   72
 32  ω    139.00 174.00   0.50    0.42    --  111.50  25.00 -11.00   70
 33  ω    -26.00  24.00   0.50    0.11    --  -48.90  25.00 -11.00  100
 34  ω    -81.00 -44.00   0.50    0.11    --  -48.90 125.00-180.00   74
 35  ω    -45.00 -18.00   0.50    0.42    --  -90.00  45.00-150.00   54
 36  ω   -116.00 -46.00   0.50    0.11    --  -48.90 -25.00-175.00  140
 37  ω   -145.00-120.00   0.50    0.42    --  -90.00 -25.00-175.00   50
;
_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      -0.2215478000
_diffrn_orient_matrix_UB_12      -0.0029845000
_diffrn_orient_matrix_UB_13      -0.0395589000
_diffrn_orient_matrix_UB_21      0.2918872000
_diffrn_orient_matrix_UB_22      -0.0459565000
_diffrn_orient_matrix_UB_23      -0.0251638000
_diffrn_orient_matrix_UB_31      -0.0974642000
_diffrn_orient_matrix_UB_32      -0.1318833000
_diffrn_orient_matrix_UB_33      0.0096723000
_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         0.0
_reflns_limit_h_max              5
_reflns_limit_h_min              -5
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              40
_reflns_limit_l_min              0
_reflns_number_gt                2819
_reflns_number_total             3100
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.3083
_refine_diff_density_min         -0.7349
_refine_diff_density_rms         0.1160
_refine_ls_d_res_high            0.7838
_refine_ls_d_res_low             10.4325
_refine_ls_goodness_of_fit_ref   1.0334
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3100
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0433
_refine_ls_restrained_S_all      1.0332
_refine_ls_shift/su_max          -0.0010
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0666P)²+1.3887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1200
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C3-C6A
 1.49 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C6) = Uanis(C6A)
4. Others
 Sof(C6A)=Sof(H6A)=1-FVAR(1)
 Sof(C6)=Sof(H6)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C10(H10), C6A(H6A)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
_atom_site_disorder_group
I1 I 0.63123(8) 0.59179(3) 0.393855(9) 0.06233(15) Uani 1.000000 . .
Cl1 Cl 0.2588(4) 0.53789(12) 0.30048(5) 0.0789(4) Uani 1.000000 . .
N1 N 0.8613(15) 0.3936(4) 0.44711(18) 0.0782(13) Uani 1.000000 . .
C1 C 0.7857(16) 0.3578(5) 0.48489(19) 0.0760(14) Uani 1.000000 . .
H1 H 0.6911(16) 0.4140(5) 0.50249(19) 0.0912(17) Uiso 1.000000 R .
Cl2 Cl 0.0087(4) 0.73781(15) 0.23872(4) 0.0819(4) Uani 1.000000 . .
C2 C 0.8386(16) 0.2423(5) 0.49967(18) 0.0728(14) Uani 1.000000 . .
H2 H 0.7797(16) 0.2216(5) 0.52648(18) 0.0874(17) Uiso 1.000000 R .
Cl3 Cl 0.4856(5) 1.08487(12) 0.33848(5) 0.0803(4) Uani 1.000000 . .
C3 C 0.9799(14) 0.1579(4) 0.47427(17) 0.0652(13) Uani 1.000000 D .
Cl4 Cl 0.7067(4) 0.89328(11) 0.40428(4) 0.0675(3) Uani 1.000000 . .
C4 C 1.0654(17) 0.1951(5) 0.4353(2) 0.0762(14) Uani 1.000000 . .
H4 H 1.1680(17) 0.1416(5) 0.4175(2) 0.0914(17) Uiso 1.000000 R .
C5 C 0.9990(18) 0.3118(5) 0.4229(2) 0.0791(15) Uani 1.000000 . .
H5 H 1.0532(18) 0.3346(5) 0.3961(2) 0.0950(18) Uiso 1.000000 R .
C6 C 1.0654(15) 0.0294(5) 0.48462(18) 0.0563(14) Uani 0.809(11) . 1
H6 H 1.2183(15) -0.0105(5) 0.46850(18) 0.0676(17) Uiso 0.809(11) R 1
C7 C 0.4706(11) 0.7226(4) 0.35058(13) 0.0525(9) Uani 1.000000 . .
C8 C 0.3165(12) 0.6884(4) 0.31314(14) 0.0561(10) Uani 1.000000 . .
C9 C 0.2107(13) 0.7781(5) 0.28470(14) 0.0599(10) Uani 1.000000 . .
C10 C 0.2584(13) 0.8976(5) 0.29297(15) 0.0611(11) Uani 1.000000 . .
H10 H 0.1835(13) 0.9557(5) 0.27406(15) 0.0733(13) Uiso 1.000000 R .
C11 C 0.4185(13) 0.9332(4) 0.32951(14) 0.0567(10) Uani 1.000000 . .
C12 C 0.5192(11) 0.8458(4) 0.35828(13) 0.0528(9) Uani 1.000000 . .
C6A C 0.931(7) 0.0551(19) 0.5044(7) 0.0563(14) Uani 0.191(11) D 2
H6A H 0.811(7) 0.0662(19) 0.5283(7) 0.0676(17) Uiso 0.191(11) R 2


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C7 2.098(4) . ?
Cl1 C8 1.723(5) . ?
N1 C1 1.322(9) . ?
N1 C5 1.326(9) . ?
C1 H1 0.9300 . ?
C1 C2 1.375(8) . ?
Cl2 C9 1.732(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(9) . ?
Cl3 C11 1.718(5) . ?
C3 C4 1.372(9) . ?
C3 C6 1.495(7) . ?
C3 C6A 1.508(16) . ?
Cl4 C12 1.729(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(8) . ?
C5 H5 0.9300 . ?
C6 C6 1.308(13) 3_756 ?
C6 H6 0.9300 . ?
C7 C8 1.396(6) . ?
C7 C12 1.394(6) . ?
C8 C9 1.408(7) . ?
C9 C10 1.357(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(7) . ?
C11 C12 1.390(6) . ?
C6A C6A 1.37(5) 3_756 ?
C6A H6A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C1 116.7(5) . . ?
H1 C1 N1 118.1(3) . . ?
C2 C1 N1 123.8(6) . . ?
C2 C1 H1 118.1(4) . . ?
H2 C2 C1 120.5(4) . . ?
C3 C2 C1 119.1(5) . . ?
C3 C2 H2 120.5(3) . . ?
C4 C3 C2 117.4(5) . . ?
C6 C3 C2 127.5(5) . . ?
C6 C3 C4 115.1(5) . . ?
C6A C3 C2 93.6(11) . . ?
C6A C3 C4 148.5(11) . . ?
C6A C3 C6 34.7(10) . . ?
H4 C4 C3 120.2(3) . . ?
C5 C4 C3 119.7(6) . . ?
C5 C4 H4 120.2(4) . . ?
C4 C5 N1 123.3(6) . . ?
H5 C5 N1 118.4(3) . . ?
H5 C5 C4 118.4(4) . . ?
C6 C6 C3 122.8(7) 3_756 . ?
H6 C6 C3 118.6(3) . . ?
C8 C7 I1 120.8(3) . . ?
C12 C7 I1 120.8(3) . . ?
C12 C7 C8 118.4(4) . . ?
C7 C8 Cl1 121.3(4) . . ?
C9 C8 Cl1 119.1(4) . . ?
C9 C8 C7 119.6(4) . . ?
C8 C9 Cl2 120.3(4) . . ?
C10 C9 Cl2 118.6(4) . . ?
C10 C9 C8 121.0(4) . . ?
H10 C10 C9 119.9(3) . . ?
C11 C10 C9 120.2(4) . . ?
C11 C10 H10 119.9(3) . . ?
C10 C11 Cl3 119.2(4) . . ?
C12 C11 Cl3 121.3(4) . . ?
C12 C11 C10 119.5(4) . . ?
C7 C12 Cl4 120.3(3) . . ?
C11 C12 Cl4 118.5(4) . . ?
C11 C12 C7 121.3(4) . . ?
C6A C6A C3 118(3) 3_756 . ?
H6A C6A C3 120.9(11) . . ?

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 C7 C8 Cl1 -1.2(4) . . . . ?
I1 C7 C8 C9 179.9(4) . . . . ?
I1 C7 C12 Cl4 -1.2(4) . . . . ?
I1 C7 C12 C11 178.9(4) . . . . ?
Cl1 C8 C7 C12 177.9(4) . . . . ?
Cl1 C8 C9 Cl2 2.9(4) . . . . ?
Cl1 C8 C9 C10 -178.4(4) . . . . ?
N1 C1 C2 C3 0.4(8) . . . . ?
N1 C5 C4 C3 1.8(8) . . . . ?
C1 C2 C3 C4 1.0(7) . . . . ?
C1 C2 C3 C6 178.3(5) . . . . ?
C1 C2 C3 C6A -173.4(12) . . . . ?
Cl2 C9 C8 C7 -178.2(4) . . . . ?
Cl2 C9 C10 C11 179.9(4) . . . . ?
C2 C3 C4 C5 -2.0(6) . . . . ?
C2 C3 C6 C6 19.7(7) . . . 3_756 ?
C2 C3 C6A C6A -173(2) . . . 3_756 ?
Cl3 C11 C10 C9 178.2(4) . . . . ?
Cl3 C11 C12 Cl4 1.5(5) . . . . ?
Cl3 C11 C12 C7 -178.7(4) . . . . ?
C3 C6 C6 C3 180.0(7) . . 3_756 3_756 ?
C3 C6A C6A C3 -180(2) . . 3_756 3_756 ?
Cl4 C12 C7 C8 179.6(4) . . . . ?
Cl4 C12 C11 C10 -178.0(4) . . . . ?
C7 C8 C9 C10 0.5(6) . . . . ?
C7 C12 C11 C10 1.8(5) . . . . ?
C8 C9 C10 C11 1.1(6) . . . . ?
C9 C10 C11 C12 -2.3(6) . . . . ?


_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 1.432
_oxdiff_exptl_absorpt_empirical_full_min 0.786
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
C3 C6A 1 1.4900 0.0200 -0.0176
_chemical_name_systematic        
'(E)-1,2-bis(4-pyridyl)ethene and 1,2,4,5-tetrachloro-3-iodobenzene cocrystal'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
_refine_special_details          
'Disordered ethylene group modelled over two positions.'
####################################################################### 
# 
# 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_eb_a_159_2_auto
_database_code_depnum_ccdc_archive 'CCDC 2264916'
loop_
_audit_author_name
_audit_author_address
'Eric Bosch'
;Missouri State University
United States of America
;
_audit_update_record             
;
2023-05-23 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_audit_creation_date             2023-05-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
loop_
_audit_author_email
?
_chemical_formula_moiety         '2(C6 H Cl4 I), C12 H8 N2'
_chemical_formula_sum            'C24 H10 Cl8 I2 N2'
_chemical_formula_weight         863.789
_chemical_oxdiff_formula         'C24 H10 Cl8 I2 N2'
_chemical_oxdiff_usercomment     'cut block'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
I -0.19206 6.94430 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07120 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   4.0163(1)
_cell_length_b                   11.2938(1)
_cell_length_c                   31.5449(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.831(1)
_cell_angle_gamma                90
_cell_volume                     1430.12(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8445
_cell_measurement_temperature    298.06(10)
_cell_measurement_theta_max      78.6730
_cell_measurement_theta_min      2.7700
_exptl_absorpt_coefficient_mu    24.313
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    2.006
_exptl_crystal_description       block
_exptl_crystal_F_000             828.223
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -2 -1 0.0644
2 -1 -2 0.0606
-2 1 2 0.0661
1 -1 2 0.0656
-1 1 -2 0.0643
0 -1 0 0.0440
0 1 0 0.0377
0 0 -1 0.0460
0 0 1 0.0220

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
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
1.0000 -2.0010 -0.9995 -0.0671 -0.2901 0.3666
2.0000 -1.0019 -2.0014 -0.0136 -0.6953 0.3595
-2.0000 1.0019 2.0014 0.0136 0.6953 -0.3595
1.0001 -1.0009 1.9996 0.1119 -0.2975 0.2773
-1.0001 1.0009 -1.9996 -0.1119 0.2975 -0.2773
0.0000 -1.0000 0.0008 -0.0402 0.0384 0.1246
-0.0000 1.0000 -0.0008 0.0402 -0.0384 -0.1246
-0.0000 -0.0000 -1.0000 -0.0463 -0.0103 -0.0118
0.0000 0.0000 1.0000 0.0463 0.0103 0.0118

_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.9996
_diffrn_reflns_Laue_measured_fraction_max 0.9942
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            14488
_diffrn_reflns_point_group_measured_fraction_full 0.9996
_diffrn_reflns_point_group_measured_fraction_max 0.9942
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         79.77
_diffrn_reflns_theta_min         2.80
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.06(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.9942
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     43.00  76.00   0.50    0.15    --  111.50 -61.00-150.00   66
  2  ω     71.00  96.00   0.50    0.15    --  111.50 -77.00  30.00   50
  3  ω     51.00  76.00   0.50    0.15    --  111.50 -61.00  60.00   50
  4  ω     63.00 108.00   0.50    0.15    --  111.50 -77.00  90.00   90
  5  ω     66.00  92.00   0.50    0.15    --  111.50 -77.00 120.00   52
  6  ω     41.00  76.00   0.50    0.15    --  111.50 -61.00 120.00   70
  7  ω     49.00  74.00   0.50    0.15    --  111.50 -61.00  30.00   50
  8  ω     47.00  75.00   0.50    0.15    --  111.50 -61.00 -30.00   56
  9  ω     49.00  74.00   0.50    0.15    --  111.50 -61.00 -60.00   50
 10  ω     40.00  72.00   0.50    0.15    --  111.50 -61.00-120.00   64
 11  ω     50.00  86.00   0.50    0.15    --  111.50 -95.00 -60.00   72
 12  ω     86.00 111.00   0.50    0.15    --  111.50-125.00-120.00   50
 13  ω     66.00 109.00   0.50    0.15    --  111.50-125.00-150.00   86
 14  ω     54.00  97.00   0.50    0.15    --  111.50-125.00-180.00   86
 15  ω     50.00  75.00   0.50    0.15    --  111.50 -95.00-150.00   50
 16  ω     40.00 101.00   0.50    0.15    --  111.50 -95.00  30.00  122
 17  ω    116.00 142.00   0.50    0.15    --  111.50  15.00 -60.00   52
 18  ω    153.00 178.00   0.50    0.15    --  111.50  77.00  90.00   50
 19  ω    142.00 176.00   0.50    0.15    --  111.50  45.00  60.00   68
 20  ω    102.00 130.00   0.50    0.15    --  111.50  45.00  60.00   56
 21  ω    103.00 169.00   0.50    0.15    --  111.50  45.00   0.00  132
 22  ω    124.00 150.00   0.50    0.15    --  111.50  45.00 150.00   52
 23  ω    144.00 172.00   0.50    0.15    --  111.50  77.00   0.00   56
 24  ω    120.00 178.00   0.50    0.15    --  111.50  32.00  35.00  116
 25  ω     56.00  81.00   0.50    0.05    --   48.90  32.00  35.00   50
 26  ω    101.00 133.00   0.50    0.15    --  111.50  30.00 150.00   64
 27  ω    106.00 166.00   0.50    0.15    --  111.50  61.00 -60.00  120
 28  ω    102.00 133.00   0.50    0.15    --  111.50  30.00 -30.00   62
 29  ω    109.00 135.00   0.50    0.15    --  111.50  30.00 -60.00   52
 30  ω    111.00 136.00   0.50    0.15    --  111.50  45.00-120.00   50
 31  ω    135.00 161.00   0.50    0.15    --  111.50  45.00-180.00   52
 32  ω    101.00 127.00   0.50    0.15    --  111.50  30.00-180.00   52
 33  ω    113.00 138.00   0.50    0.15    --  111.50 125.00 -60.00   50
 34  ω    153.00 178.00   0.50    0.15    --  111.50 125.00 -60.00   50
 35  ω    -14.00  11.00   0.50    0.05    --   48.90 -32.00-123.00   50
 36  ω     -8.00  25.00   0.50    0.05    --  -48.90  19.00  60.00   66
 37  ω    -32.00  -7.00   0.50    0.05    --  -48.90  32.00  35.00   50
 38  ω    -80.00 -55.00   0.50    0.05    --  -48.90 125.00-180.00   50
 39  ω    -44.00 -18.00   0.50    0.15    --  -90.00  45.00-150.00   52
 40  ω    -37.00  23.00   0.50    0.05    --  -48.90  38.00-180.00  120
 41  ω   -122.00 -40.00   0.50    0.05    --  -48.90 -32.00-123.00  164
 42  ω   -145.00-120.00   0.50    0.15    --  -90.00 -32.00-123.00   50
;
_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      0.0596685000
_diffrn_orient_matrix_UB_12      0.0402368000
_diffrn_orient_matrix_UB_13      0.0462788000
_diffrn_orient_matrix_UB_21      -0.3565330000
_diffrn_orient_matrix_UB_22      -0.0383664000
_diffrn_orient_matrix_UB_23      0.0103251000
_diffrn_orient_matrix_UB_31      0.1291181000
_diffrn_orient_matrix_UB_32      -0.1245548000
_diffrn_orient_matrix_UB_33      0.0117638000
_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         0.0
_reflns_limit_h_max              5
_reflns_limit_h_min              -5
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              40
_reflns_limit_l_min              0
_reflns_number_gt                2900
_reflns_number_total             3089
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.5045
_refine_diff_density_min         -1.0510
_refine_diff_density_rms         0.1171
_refine_ls_d_res_high            0.7834
_refine_ls_d_res_low             15.7644
_refine_ls_goodness_of_fit_ref   1.0274
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    10
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3089
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.0274
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0514P)²+1.2404P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0893
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C10(H10), C2(H2), C4(H4), C3(H3)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
I1 I 0.35601(6) 0.596626(18) 0.606745(7) 0.04195(10) Uani 1.000000 .
Cl4 Cl 0.2946(3) 0.89148(7) 0.59280(3) 0.0488(2) Uani 1.000000 .
Cl3 Cl 0.5199(3) 1.08190(8) 0.65881(3) 0.0580(3) Uani 1.000000 .
Cl1 Cl 0.7281(3) 0.54965(9) 0.70247(3) 0.0592(3) Uani 1.000000 .
Cl2 Cl 0.9830(3) 0.74767(11) 0.76446(3) 0.0657(3) Uani 1.000000 .
C7 C 0.5220(8) 0.7269(3) 0.64987(10) 0.0341(6) Uani 1.000000 .
C12 C 0.4781(8) 0.8476(3) 0.64036(9) 0.0350(6) Uani 1.000000 .
N1 N 0.1346(12) 0.3974(3) 0.55307(14) 0.0580(10) Uani 1.000000 .
C11 C 0.5834(9) 0.9341(3) 0.66929(10) 0.0386(7) Uani 1.000000 .
C5 C 0.0554(9) 0.1673(3) 0.52290(11) 0.0374(7) Uani 1.000000 .
C6 C 0.0166(10) 0.0489(3) 0.50669(11) 0.0422(7) Uani 1.000000 .
C1 C 0.1782(11) 0.2558(3) 0.49709(12) 0.0446(8) Uani 1.000000 .
H1 H 0.2378(11) 0.2397(3) 0.46943(12) 0.0535(9) Uiso 1.000000 R
C10 C 0.7375(10) 0.9017(3) 0.70733(11) 0.0444(8) Uani 1.000000 .
H10 H 0.8087(10) 0.9596(3) 0.72650(11) 0.0533(10) Uiso 1.000000 R
C2 C 0.2092(12) 0.3688(3) 0.51384(14) 0.0526(10) Uani 1.000000 .
H2 H 0.2873(12) 0.4283(3) 0.49639(14) 0.0631(12) Uiso 1.000000 R
C8 C 0.6749(9) 0.6961(3) 0.68866(11) 0.0393(7) Uani 1.000000 .
C9 C 0.7859(9) 0.7844(4) 0.71693(10) 0.0423(7) Uani 1.000000 .
C4 C -0.0332(12) 0.1956(3) 0.56351(13) 0.0528(9) Uani 1.000000 .
H4 H -0.1238(12) 0.1387(3) 0.58107(13) 0.0634(11) Uiso 1.000000 R
C3 C 0.0157(14) 0.3103(4) 0.57752(15) 0.0616(11) Uani 1.000000 .
H3 H -0.0362(14) 0.3284(4) 0.60530(15) 0.0739(14) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C7 2.098(3) . ?
Cl4 C12 1.723(3) . ?
Cl3 C11 1.719(4) . ?
Cl1 C8 1.722(4) . ?
Cl2 C9 1.724(3) . ?
C7 C12 1.405(5) . ?
C7 C8 1.396(4) . ?
C12 C11 1.393(5) . ?
N1 C2 1.323(6) . ?
N1 C3 1.346(6) . ?
C11 C10 1.382(5) . ?
C5 C6 1.439(4) . ?
C5 C1 1.389(5) . ?
C5 C4 1.378(5) . ?
C6 C6 1.189(7) 3_556 ?
C1 H1 0.9300 . ?
C1 C2 1.385(5) . ?
C10 H10 0.9300 . ?
C10 C9 1.371(5) . ?
C2 H2 0.9300 . ?
C8 C9 1.401(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.381(6) . ?
C3 H3 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
C12 C7 I1 120.4(2) . . ?
C8 C7 I1 121.0(3) . . ?
C8 C7 C12 118.6(3) . . ?
C7 C12 Cl4 120.8(2) . . ?
C11 C12 Cl4 118.8(3) . . ?
C11 C12 C7 120.5(3) . . ?
C3 N1 C2 116.9(3) . . ?
C12 C11 Cl3 121.0(3) . . ?
C10 C11 Cl3 119.0(3) . . ?
C10 C11 C12 120.0(3) . . ?
C1 C5 C6 119.8(3) . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 C1 119.0(3) . . ?
C6 C6 C5 179.8(6) 3_556 . ?
H1 C1 C5 121.0(2) . . ?
C2 C1 C5 117.9(4) . . ?
C2 C1 H1 121.0(2) . . ?
H10 C10 C11 119.8(2) . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10 119.8(2) . . ?
C1 C2 N1 124.2(4) . . ?
H2 C2 N1 117.9(2) . . ?
H2 C2 C1 117.9(2) . . ?
C7 C8 Cl1 120.6(3) . . ?
C9 C8 Cl1 119.2(3) . . ?
C9 C8 C7 120.1(3) . . ?
C10 C9 Cl2 118.9(3) . . ?
C8 C9 Cl2 120.7(3) . . ?
C8 C9 C10 120.5(3) . . ?
H4 C4 C5 120.8(2) . . ?
C3 C4 C5 118.5(4) . . ?
C3 C4 H4 120.8(3) . . ?
C4 C3 N1 123.4(4) . . ?
H3 C3 N1 118.3(2) . . ?
H3 C3 C4 118.3(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C7 C12 Cl4 -1.2(3) . . . . ?
I1 C7 C12 C11 178.9(3) . . . . ?
I1 C7 C8 Cl1 -0.6(3) . . . . ?
I1 C7 C8 C9 179.6(3) . . . . ?
Cl4 C12 C7 C8 179.4(3) . . . . ?
Cl4 C12 C11 Cl3 2.2(3) . . . . ?
Cl4 C12 C11 C10 -178.7(3) . . . . ?
Cl3 C11 C12 C7 -178.0(3) . . . . ?
Cl3 C11 C10 C9 178.8(3) . . . . ?
Cl1 C8 C7 C12 178.7(3) . . . . ?
Cl1 C8 C9 Cl2 1.6(3) . . . . ?
Cl1 C8 C9 C10 -178.0(3) . . . . ?
Cl2 C9 C10 C11 179.3(3) . . . . ?
Cl2 C9 C8 C7 -178.6(3) . . . . ?
C7 C12 C11 C10 1.2(4) . . . . ?
C7 C8 C9 C10 1.8(4) . . . . ?
C12 C11 C10 C9 -0.4(4) . . . . ?
N1 C2 C1 C5 1.2(6) . . . . ?
N1 C3 C4 C5 2.5(6) . . . . ?
C11 C10 C9 C8 -1.1(5) . . . . ?


_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 1.849
_oxdiff_exptl_absorpt_empirical_full_min 0.696
####################################################################### 
# 
# 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_3_eb_a_158_3
_database_code_depnum_ccdc_archive 'CCDC 2264917'
loop_
_audit_author_name
_audit_author_address
'Eric Bosch'
;Missouri State University
United States of America
;
_audit_update_record             
;
2023-05-23 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_audit_creation_date             2023-04-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
loop_
_audit_author_email
?
_chemical_formula_moiety         'C10 H8 N4, 2(C6 H Cl4 I)'
_chemical_formula_sum            'C22 H10 Cl8 I2 N4'
_chemical_formula_weight         867.781
_chemical_oxdiff_formula         'C24 H10 Cl8 I2 N4'
_chemical_oxdiff_usercomment     'cut block'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
I -0.19206 6.94430 20.14720 18.99490 7.51380 2.27350 4.34700 0.38140 27.76600
66.87760 4.07120 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   4.0199(1)
_cell_length_b                   10.8882(3)
_cell_length_c                   32.3284(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.490(3)
_cell_angle_gamma                90
_cell_volume                     1414.52(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7693
_cell_measurement_temperature    298.36(16)
_cell_measurement_theta_max      79.0370
_cell_measurement_theta_min      4.8800
_exptl_absorpt_coefficient_mu    24.605
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.037
_exptl_crystal_description       block
_exptl_crystal_F_000             832.276
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 2 2 0.0477
0 1 -2 0.0425
0 0 1 0.0171
0 0 -1 0.0446
0 -1 -2 0.0259
0 1 2 0.0471
2 -1 2 0.0716
-1 -2 0 0.0447
0 -1 1 0.0322
1 0 -2 0.0696

_exptl_crystal_preparation       'from pure components'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
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
-1.0003 2.0027 2.0022 -0.0796 -0.2636 0.3986
-0.0002 1.0005 -1.9998 -0.0021 0.0943 0.1423
-0.0001 -0.0001 1.0003 0.0302 -0.0361 -0.0076
0.0001 0.0001 -1.0003 -0.0302 0.0361 0.0076
0.0005 -1.0002 -2.0014 -0.1187 0.0501 -0.1120
-0.0005 1.0002 2.0014 0.1187 -0.0501 0.1120
1.9992 -1.0046 1.9997 0.5151 0.3769 -0.4613
-0.9989 -1.9986 -0.0016 -0.3730 -0.2799 -0.0947
0.0002 -1.0004 0.9995 -0.0281 -0.0582 -0.1347
0.9997 -0.0020 -2.0006 0.1961 0.3079 -0.1444

_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.9961
_diffrn_reflns_Laue_measured_fraction_max 0.9782
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            12094
_diffrn_reflns_point_group_measured_fraction_full 0.9961
_diffrn_reflns_point_group_measured_fraction_max 0.9782
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         79.95
_diffrn_reflns_theta_min         2.73
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.36(16)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9961
_diffrn_measured_fraction_theta_max 0.9782
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    124.00 161.00   0.50    0.65    --  111.50 125.00-180.00   74
  2  ω    123.00 159.00   0.50    0.65    --  111.50 125.00  30.00   72
  3  ω    -34.00  11.00   0.50    0.16    --  -48.65  35.00 -80.00   90
  4  ω    -62.00 -35.00   0.50    0.65    --  -90.00  61.00  90.00   54
  5  ω    -20.00  21.00   0.50    0.16    --  -48.65  19.00  60.00   82
  6  ω     10.00  38.00   0.50    0.16    --   48.65 -35.00 122.00   56
  7  ω    122.00 157.00   0.50    0.65    --  111.50  77.00 -30.00   70
  8  ω    112.00 146.00   0.50    0.65    --  111.50  61.00-120.00   68
  9  ω    118.00 144.00   0.50    0.65    --  111.50  61.00-150.00   52
 10  ω    107.00 144.00   0.50    0.65    --  111.50  61.00-180.00   74
 11  ω    108.00 178.00   0.50    0.65    --  111.50  45.00 -60.00  140
 12  ω    103.00 136.00   0.50    0.65    --  111.50  45.00-150.00   66
 13  ω    102.00 127.00   0.50    0.65    --  111.50  45.00-120.00   50
 14  ω    130.00 156.00   0.50    0.65    --  111.50  35.00 -80.00   52
 15  ω    142.00 173.00   0.50    0.65    --  111.50  45.00 120.00   62
 16  ω    103.00 137.00   0.50    0.65    --  111.50  45.00 120.00   68
 17  ω    114.00 145.00   0.50    0.65    --  111.50  61.00 150.00   62
 18  ω    153.00 178.00   0.50    0.65    --  111.50  61.00 150.00   50
 19  ω    127.00 168.00   0.50    0.65    --  111.50  30.00 150.00   82
 20  ω     56.00  81.00   0.50    0.16    --   48.65  35.00 -80.00   50
 21  ω     40.00  65.00   0.50    0.65    --  111.50 -61.00 -30.00   50
 22  ω     44.00  82.00   0.50    0.65    --  111.50 -77.00-120.00   76
 23  ω     84.00 110.00   0.50    0.65    --  111.50 -77.00 -90.00   52
 24  ω     40.00  76.00   0.50    0.65    --  111.50 -61.00 -90.00   72
 25  ω     40.00  65.00   0.50    0.65    --  111.50 -61.00-150.00   50
 26  ω     62.00  88.00   0.50    0.65    --  111.50 -77.00 -30.00   52
 27  ω     42.00  67.00   0.50    0.65    --  111.50 -61.00   0.00   50
 28  ω     47.00  73.00   0.50    0.65    --  111.50 -77.00  30.00   52
 29  ω     46.00  71.00   0.50    0.65    --  111.50 -61.00  30.00   50
 30  ω     49.00  76.00   0.50    0.65    --  111.50 -61.00  90.00   54
 31  ω     43.00  68.00   0.50    0.65    --  111.50 -95.00  90.00   50
 32  ω     41.00  67.00   0.50    0.65    --  111.50 -95.00 120.00   52
 33  ω     69.00  99.00   0.50    0.65    --  111.50 -95.00 120.00   60
 34  ω     71.00  99.00   0.50    0.65    --  111.50 -95.00  90.00   56
 35  ω    102.00 128.00   0.50    0.65    --  111.50 -87.00   8.27   52
 36  ω     94.00 120.00   0.50    0.65    --  111.50 -84.00 148.34   52
 37  ω     53.00  82.00   0.50    0.65    --  111.50 -87.00   8.27   58
 38  ω     66.00  92.00   0.50    0.65    --  111.50 -95.00 -30.00   52
 39  ω     71.00 105.00   0.50    0.65    --  111.50 -95.00-120.00   68
 40  ω     49.00  76.00   0.50    0.65    --  111.50 -95.00-180.00   54
 41  ω   -101.00 -40.00   0.50    0.16    --  -48.65 -38.00  60.00  122
 42  ω    -97.00 -39.00   0.50    0.16    --  -48.65 -35.00 122.00  116
 43  ω   -121.00 -96.00   0.50    0.65    --  -90.00 -35.00 122.00   50
;
_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      0.2567323000
_diffrn_orient_matrix_UB_12      0.0582957000
_diffrn_orient_matrix_UB_13      0.0302163000
_diffrn_orient_matrix_UB_21      0.2357962000
_diffrn_orient_matrix_UB_22      0.0222213000
_diffrn_orient_matrix_UB_23      -0.0360822000
_diffrn_orient_matrix_UB_31      -0.1593399000
_diffrn_orient_matrix_UB_32      0.1270312000
_diffrn_orient_matrix_UB_33      -0.0075703000
_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         0.0
_reflns_limit_h_max              5
_reflns_limit_h_min              -5
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              41
_reflns_limit_l_min              0
_reflns_number_gt                2690
_reflns_number_total             3011
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         1.8540
_refine_diff_density_min         -1.4139
_refine_diff_density_rms         0.2646
_refine_ls_d_res_high            0.7829
_refine_ls_d_res_low             16.1587
_refine_ls_goodness_of_fit_ref   1.0388
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    15
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3011
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0673
_refine_ls_restrained_S_all      1.0385
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0563P)²+21.0115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1769
_refine_ls_wR_factor_ref         0.1800
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C5-N2
 1.43 with sigma of 0.02
 C5A-N2A
 1.43 with sigma of 0.02
3. Others
 Sof(N2A)=Sof(C5A)=1-FVAR(1)
 Sof(N2)=Sof(C5)=FVAR(1)
 Fixed Sof: H1a(0.5) H1b(0.5) H4a(0.5) H4b(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1a), C1(H1b), C2(H2), C3(H3), C4(H4a), C4(H4b), C9(H9)
;
# start Validation Reply Form
_vrf_PLAT234_3_eb_a_158_3        
;
PROBLEM: Large Hirshfeld Difference C4       --C5A      .       0.26 Ang.  
RESPONSE: In the pyridyl ring the ipso C attached to the azo group (C5) was
modelled over two positions while bonded C1 and C4 were not.  Elongated C1 
and C4 are clearly both also  disordered over two positions however 
modelling them over two positions was unstable without multiple additional 
restraints.  Consequently the Hirshfeld Difference is understandable.
;
# end Validation Reply Form
_atom_sites_solution_primary     direct
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_refinement_flags_posn
_atom_site_disorder_group
I1 I 0.14882(16) 0.91643(6) 0.393374(19) 0.0486(2) Uani 1.000000 . .
Cl1 Cl 0.2104(7) 0.6108(2) 0.40469(7) 0.0521(6) Uani 1.000000 . .
N1 N 0.382(3) 0.1162(7) 0.4490(3) 0.057(2) Uani 1.000000 . .
C1 C 0.333(3) 0.2601(14) 0.5039(4) 0.067(3) Uani 1.000000 . .
H1a H 0.259(3) 0.2709(14) 0.5307(4) 0.081(4) Uiso 0.500000 R 1
H1b H 0.268(3) 0.2792(14) 0.5305(4) 0.081(4) Uiso 0.500000 R 2
Cl2 Cl -0.0358(9) 0.4166(2) 0.34045(9) 0.0664(8) Uani 1.000000 . .
N2 N 0.462(6) 0.457(3) 0.5101(9) 0.045(9) Uani 0.49(8) D 1
C2 C 0.301(3) 0.1438(10) 0.4869(4) 0.060(3) Uani 1.000000 . .
H2 H 0.217(3) 0.0816(10) 0.5033(4) 0.072(3) Uiso 1.000000 R .
Cl3 Cl -0.4803(8) 0.7690(3) 0.23882(8) 0.0674(8) Uani 1.000000 . .
C3 C 0.514(4) 0.2050(11) 0.4272(4) 0.066(3) Uani 1.000000 . .
H3 H 0.580(4) 0.1868(11) 0.4005(4) 0.080(4) Uiso 1.000000 R .
Cl4 Cl -0.2202(8) 0.9712(3) 0.30006(9) 0.0638(7) Uani 1.000000 . .
C4 C 0.562(3) 0.3241(11) 0.4416(5) 0.069(4) Uani 1.000000 . .
H4a H 0.654(3) 0.3866(11) 0.4260(5) 0.083(4) Uiso 0.500000 R 1
H4b H 0.657(3) 0.3818(11) 0.4243(5) 0.083(4) Uiso 0.500000 R 2
C5 C 0.440(14) 0.342(5) 0.4881(12) 0.046(9) Uani 0.49(8) D 1
C6 C -0.018(2) 0.7842(9) 0.3504(3) 0.041(2) Uani 1.000000 . .
C7 C 0.020(2) 0.6602(9) 0.3589(3) 0.0381(18) Uani 1.000000 . .
C8 C -0.089(3) 0.5712(9) 0.3309(3) 0.047(2) Uani 1.000000 . .
C9 C -0.244(2) 0.6062(10) 0.2936(3) 0.046(2) Uani 1.000000 . .
H9 H -0.319(2) 0.5473(10) 0.2747(3) 0.056(3) Uiso 1.000000 R .
C10 C -0.284(3) 0.7278(10) 0.2853(3) 0.047(2) Uani 1.000000 . .
C11 C -0.172(2) 0.8180(9) 0.3129(3) 0.043(2) Uani 1.000000 . .
N2A N 0.548(6) 0.482(3) 0.4833(9) 0.054(9) Uani 0.51(8) D 2
C5A C 0.485(10) 0.354(3) 0.4747(14) 0.038(7) Uani 0.51(8) D 2


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 C6 2.100(8) . ?
Cl1 C7 1.733(9) . ?
N1 C2 1.310(15) . ?
N1 C3 1.317(16) . ?
C1 H1a 0.9300 . ?
C1 H1b 0.9300 . ?
C1 C2 1.385(17) . ?
C1 C5 1.12(6) . ?
C1 C5A 1.53(3) . ?
Cl2 C8 1.724(10) . ?
N2 N2 1.19(6) 3_666 ?
N2 C5 1.436(17) . ?
C2 H2 0.9300 . ?
Cl3 C10 1.738(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(17) . ?
Cl4 C11 1.728(10) . ?
C4 H4a 0.9300 . ?
C4 H4b 0.9300 . ?
C4 C5 1.61(4) . ?
C4 C5A 1.17(5) . ?
C6 C7 1.386(14) . ?
C6 C11 1.396(13) . ?
C7 C8 1.391(13) . ?
C8 C9 1.395(14) . ?
C9 H9 0.9300 . ?
C9 C10 1.359(15) . ?
C10 C11 1.392(14) . ?
N2A N2A 1.22(7) 3_666 ?
N2A C5A 1.439(17) . ?

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
C3 N1 C2 116.5(9) . . ?
H1b C1 H1a 5.9 . . ?
C2 C1 H1a 117.3(8) . . ?
C2 C1 H1b 123.2(8) . . ?
C5 C1 H1a 117.3(16) . . ?
C5 C1 H1b 111.4(16) . . ?
C5 C1 C2 125.4(18) . . ?
C5A C1 H1a 129.1(18) . . ?
C5A C1 H1b 123.2(18) . . ?
C5A C1 C2 114(2) . . ?
C5A C1 C5 12(3) . . ?
C1 C2 N1 124.0(11) . . ?
H2 C2 N1 118.0(6) . . ?
H2 C2 C1 118.0(8) . . ?
H3 C3 N1 118.0(6) . . ?
C4 C3 N1 124.0(12) . . ?
C4 C3 H3 118.0(8) . . ?
H4a C4 C3 123.7(8) . . ?
H4b C4 C3 118.9(8) . . ?
H4b C4 H4a 4.8 . . ?
C5 C4 C3 113(2) . . ?
C5 C4 H4a 124(2) . . ?
C5 C4 H4b 128(2) . . ?
C5A C4 C3 122.2(17) . . ?
C5A C4 H4a 114.1(15) . . ?
C5A C4 H4b 118.9(15) . . ?
C5A C4 C5 10(3) . . ?
N2 C5 C1 119(3) . . ?
C4 C5 C1 117(3) . . ?
C4 C5 N2 124(4) . . ?
C7 C6 I1 120.2(6) . . ?
C11 C6 I1 121.4(7) . . ?
C11 C6 C7 118.4(8) . . ?
C6 C7 Cl1 121.2(7) . . ?
C8 C7 Cl1 117.8(7) . . ?
C8 C7 C6 121.1(8) . . ?
C7 C8 Cl2 121.8(7) . . ?
C9 C8 Cl2 118.2(8) . . ?
C9 C8 C7 119.9(9) . . ?
H9 C9 C8 120.5(6) . . ?
C10 C9 C8 119.0(9) . . ?
C10 C9 H9 120.5(6) . . ?
C9 C10 Cl3 118.1(8) . . ?
C11 C10 Cl3 120.2(8) . . ?
C11 C10 C9 121.8(9) . . ?
C6 C11 Cl4 120.4(8) . . ?
C10 C11 Cl4 119.7(7) . . ?
C10 C11 C6 119.9(9) . . ?
C4 C5A C1 120(3) . . ?
N2A C5A C1 127(3) . . ?
N2A C5A C4 113(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C6 C7 Cl1 -0.7(8) . . . . ?
I1 C6 C7 C8 179.9(7) . . . . ?
I1 C6 C11 Cl4 1.8(8) . . . . ?
I1 C6 C11 C10 -179.1(7) . . . . ?
Cl1 C7 C6 C11 179.8(8) . . . . ?
Cl1 C7 C8 Cl2 -0.7(8) . . . . ?
Cl1 C7 C8 C9 179.8(8) . . . . ?
N1 C2 C1 C5 -3(4) . . . . ?
N1 C2 C1 C5A -2(2) . . . . ?
N1 C3 C4 C5 0(3) . . . . ?
N1 C3 C4 C5A -0(3) . . . . ?
C1 C5 N2 N2 -171(4) . . . 3_666 ?
C1 C5 C4 C3 0(5) . . . . ?
C1 C5 C4 C5A 178(12) . . . . ?
C1 C5A C4 C3 1(4) . . . . ?
C1 C5A C4 C5 -2(9) . . . . ?
C1 C5A N2A N2A -4(4) . . . 3_666 ?
Cl2 C8 C7 C6 178.7(8) . . . . ?
Cl2 C8 C9 C10 -179.2(8) . . . . ?
N2 N2 C5 C4 9(4) 3_666 . . . ?
N2 C5 C4 C3 -180(3) . . . . ?
N2 C5 C4 C5A -2(10) . . . . ?
Cl3 C10 C9 C8 -179.7(8) . . . . ?
Cl3 C10 C11 Cl4 -1.5(9) . . . . ?
Cl3 C10 C11 C6 179.3(8) . . . . ?
C3 C4 C5A N2A -179(3) . . . . ?
Cl4 C11 C6 C7 -178.7(8) . . . . ?
Cl4 C11 C10 C9 178.2(8) . . . . ?
C4 C5A N2A N2A 176(3) . . . 3_666 ?
C6 C7 C8 C9 -0.8(11) . . . . ?
C6 C11 C10 C9 -1.0(11) . . . . ?
C7 C8 C9 C10 0.3(12) . . . . ?
C8 C9 C10 C11 0.6(12) . . . . ?


_olex2_exptl_crystal_mounting_method 'in Paratone oil on a mitagen mount'
_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 2.101
_oxdiff_exptl_absorpt_empirical_full_min 0.452
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
C5 N2 1 1.4300 0.0200 -0.0056
C5A N2A 1 1.4300 0.0200 -0.0092






_refine_special_details          
'Disordered azo group and ipso C modelled over two positions.'
