# 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 2019

####################################################################### 
# 
# 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_eb884290
_audit_block_doi                 10.5517/ccdc.csd.cc223fj5
_database_code_depnum_ccdc_archive 'CCDC 1909926'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.cgd.9b00275 2019
loop_
_audit_author_name
_audit_author_address
'Eric Bosch'
;Chemistry Department, Missouri State University
United States of America
;
_audit_update_record             
;
2019-04-13 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            
'Cocrystal 1,2,4,5-tetrachlorobenzene and 1,2-bis(4-pyridyl)ethyne'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 N2, C6 Cl4 I2'
_chemical_formula_sum            'C18 H8 Cl4 I2 N2'
_chemical_formula_weight         647.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   4.0598(6)
_cell_length_b                   11.1929(18)
_cell_length_c                   12.2066(18)
_cell_angle_alpha                111.485(3)
_cell_angle_beta                 90.699(2)
_cell_angle_gamma                97.282(2)
_cell_volume                     510.94(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    5104
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      27.29

_exptl_crystal_description       'cut plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.106
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.03
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_max          0.30
_exptl_absorpt_coefficient_mu    3.606
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.693
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS V2014(Bruker AXS)'
_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3660

_diffrn_reflns_number            6470
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.797
_diffrn_reflns_theta_max         27.293
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2292
_reflns_number_gt                2189
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'XSeed (Barbour, 2001)'
_computing_publication_material  'XSeed (Barbour, 2001)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0126P)²+0.3348P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2292
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0166
_refine_ls_R_factor_gt           0.0155
_refine_ls_wR_factor_ref         0.0359
_refine_ls_wR_factor_gt          0.0353
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.71473(3) 0.70985(2) 0.29449(2) 0.03607(5) Uani 1 1 d . . . . .
Cl1 Cl 0.41080(16) 0.74935(5) 0.55783(5) 0.04710(13) Uani 1 1 d . . . . .
N1 N 0.8747(5) 0.45386(17) 0.14770(18) 0.0463(4) Uani 1 1 d . . . . .
C1 C 0.8087(6) 0.2460(2) -0.00911(19) 0.0409(5) Uani 1 1 d . . . . .
H1 H 0.736796 0.195704 -0.086961 0.049 Uiso 1 1 calc R U . . .
Cl2 Cl 0.22158(15) 1.00221(5) 0.73701(4) 0.04552(13) Uani 1 1 d . . . . .
C2 C 0.7769(6) 0.3764(2) 0.0374(2) 0.0445(5) Uani 1 1 d . . . . .
H2 H 0.681811 0.411916 -0.011211 0.053 Uiso 1 1 calc R U . . .
C3 C 1.0108(7) 0.4008(2) 0.2157(2) 0.0484(5) Uani 1 1 d . . . . .
H3 H 1.081136 0.453876 0.292995 0.058 Uiso 1 1 calc R U . . .
C4 C 1.0536(6) 0.2716(2) 0.17801(19) 0.0434(5) Uani 1 1 d . . . . .
H4 H 1.149605 0.238902 0.228705 0.052 Uiso 1 1 calc R U . . .
C5 C 0.9493(5) 0.19157(18) 0.06216(18) 0.0342(4) Uani 1 1 d . . . . .
C6 C 0.9853(6) 0.05605(19) 0.01818(19) 0.0389(4) Uani 1 1 d . . . . .
C7 C 0.5883(4) 0.88358(17) 0.41755(16) 0.0291(4) Uani 1 1 d . . . . .
C8 C 0.4624(5) 0.88740(18) 0.52420(16) 0.0304(4) Uani 1 1 d . . . . .
C9 C 0.3751(5) 1.00258(18) 0.60598(16) 0.0302(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C7 2.1056(18) . ?
Cl1 C8 1.7277(19) . ?
N1 C2 1.329(3) . ?
N1 C3 1.334(3) . ?
C1 C2 1.383(3) . ?
C1 C5 1.385(3) . ?
Cl2 C9 1.7249(19) . ?
C3 C4 1.383(3) . ?
C4 C5 1.394(3) . ?
C5 C6 1.439(3) . ?
C6 C6 1.190(4) 2_755 ?
C7 C8 1.392(3) . ?
C7 C9 1.396(3) 2_676 ?
C8 C9 1.402(3) . ?

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 N1 C3 117.09(18) . . ?
C2 C1 C5 118.9(2) . . ?
N1 C2 C1 123.7(2) . . ?
N1 C3 C4 123.9(2) . . ?
C3 C4 C5 118.3(2) . . ?
C1 C5 C4 118.12(18) . . ?
C1 C5 C6 121.03(19) . . ?
C4 C5 C6 120.86(19) . . ?
C6 C6 C5 179.9(4) 2_755 . ?
C8 C7 C9 118.27(16) . 2_676 ?
C8 C7 I1 120.69(13) . . ?
C9 C7 I1 121.03(13) 2_676 . ?
C7 C8 C9 120.90(17) . . ?
C7 C8 Cl1 120.28(14) . . ?
C9 C8 Cl1 118.82(15) . . ?
C7 C9 C8 120.82(17) 2_676 . ?
C7 C9 Cl2 120.12(14) 2_676 . ?
C8 C9 Cl2 119.06(15) . . ?

_refine_diff_density_max         0.588
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.062


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

data_hut19_48_230
_database_code_depnum_ccdc_archive 'CCDC 1954974'
loop_
_audit_author_name
_audit_author_address
'Daniel K. Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-09-20 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT250_hut19_48_230        
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.7 Note  
RESPONSE: Due to the pedal motion of molecules within the structure.
;
_vrf_PLAT431_hut19_48_230        
;
PROBLEM: Short Inter HL..A Contact  Cl1      ..N2B      .       3.12 Ang.  
RESPONSE: A feature of the structure.
;
_vrf_PLAT911_hut19_48_230        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          8 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2019-09-05T11:50:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C16 H8 Cl4 I2 N4'
_chemical_formula_weight         651.86

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.03260(16)
_cell_length_b                   10.8287(3)
_cell_length_c                   12.3790(3)
_cell_angle_alpha                111.495(3)
_cell_angle_beta                 92.054(3)
_cell_angle_gamma                94.675(3)
_cell_volume                     500.03(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    9826
_cell_measurement_theta_min      3.811
_cell_measurement_theta_max      77.026

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.054
_exptl_crystal_density_diffrn    2.165
_exptl_crystal_F_000             306
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 6 1 0.0747
2 3 -2 0.0542
3 0 1 0.0594
0 -6 -1 0.0462
0 -4 8 0.0381
-3 0 -1 0.0276
0 7 -3 0.0515
0 4 -8 0.0132
1 3 5 0.062
0 -5 7 0.0339
0 1 -8 0.0283
2 4 2 0.0644


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    29.697
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.58a (Rigaku Oxford Diffraction, 2019)
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_correction_T_min  0.068
_exptl_absorpt_correction_T_max  0.473
_shelx_estimated_absorpt_T_min   0.101
_shelx_estimated_absorpt_T_max   0.297

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      230(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.1507274
_diffrn_orient_matrix_ub_12      0.1446654
_diffrn_orient_matrix_ub_13      0.0679249
_diffrn_orient_matrix_ub_21      0.0581281
_diffrn_orient_matrix_ub_22      0.0187301
_diffrn_orient_matrix_ub_23      -0.1156119
_diffrn_orient_matrix_ub_31      -0.3486603
_diffrn_orient_matrix_ub_32      0.0484219
_diffrn_orient_matrix_ub_33      -0.0003821
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_number            16476
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.847
_diffrn_reflns_theta_max         77.116
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.956
_reflns_Friedel_coverage         0
_reflns_number_total             2016
_reflns_number_gt                1930
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0559P)²+0.6428P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2016
_refine_ls_number_parameters     159
_refine_ls_number_restraints     343
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0913
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.151
_refine_diff_density_min         -1.249
_refine_diff_density_rms         0.159

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 The 4,4'-azopyridine molecule is undergoing detectable pedal motion at
 this temperature. The major and minor positions of the disorder (A and B sites)  
 were allowed to refine their occupancies to a total value of 1. The A and B
 sites had occupancies of 0.56 and 0.44, respectively. To help model this 
 disorder and maintain reasonable ADP values SIMU, RIGU, DFIX and AFIX 
 restraints and constraints were applied. During the final refinements the 
 inconsistent reflections 3 -9 9, 4 -8 6, 0 12 0, -4 -5 8, and -3 10 1, were 
 omitted. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.77211(7) 0.29494(2) 0.20978(2) 0.03711(14) Uani 1 1 d . . . . .
Cl1 Cl 0.7164(3) -0.00716(12) 0.22818(9) 0.0438(3) Uani 1 1 d . . . . .
Cl2 Cl 0.9189(4) -0.26476(11) 0.04580(10) 0.0468(3) Uani 1 1 d . . . . .
C1 C 0.9081(11) 0.1185(4) 0.0843(4) 0.0320(9) Uani 1 1 d . . . . .
C2 C 0.8751(11) -0.0019(4) 0.1025(4) 0.0317(9) Uani 1 1 d . . . . .
C3 C 0.9646(11) -0.1183(4) 0.0192(4) 0.0325(9) Uani 1 1 d . . . . .
N1A N 0.607(3) 0.5576(6) 0.3667(9) 0.0391(17) Uani 0.558(14) 1 d G U P A 1
C4A C 0.445(3) 0.5990(8) 0.2868(6) 0.0390(17) Uani 0.558(14) 1 d G U P A 1
H4A H 0.371783 0.536938 0.212273 0.047 Uiso 0.558(14) 1 calc R U P A 1
C5A C 0.391(3) 0.7323(9) 0.3172(8) 0.0405(19) Uani 0.558(14) 1 d G U P A 1
H5A H 0.280968 0.760373 0.263175 0.049 Uiso 0.558(14) 1 calc R U P A 1
C6A C 0.498(3) 0.8242(6) 0.4274(9) 0.0381(17) Uani 0.558(14) 1 d DG U P A 1
C7A C 0.660(3) 0.7827(7) 0.5072(6) 0.0386(19) Uani 0.558(14) 1 d G U P A 1
H7A H 0.733189 0.844809 0.58178 0.046 Uiso 0.558(14) 1 calc R U P A 1
C8A C 0.714(3) 0.6494(8) 0.4769(8) 0.0421(19) Uani 0.558(14) 1 d G U P A 1
H8A H 0.824007 0.621375 0.53088 0.051 Uiso 0.558(14) 1 calc R U P A 1
N2A N 0.444(2) 0.9615(9) 0.4518(8) 0.0401(19) Uani 0.558(14) 1 d D U P A 1
N1B N 0.569(5) 0.5559(8) 0.3515(12) 0.045(2) Uani 0.442(14) 1 d G U P A 2
C4B C 0.427(4) 0.6294(12) 0.2938(8) 0.047(2) Uani 0.442(14) 1 d G U P A 2
H4B H 0.337161 0.586736 0.216603 0.056 Uiso 0.442(14) 1 calc R U P A 2
C5B C 0.419(3) 0.7661(11) 0.3504(11) 0.041(2) Uani 0.442(14) 1 d G U P A 2
H5B H 0.322557 0.815793 0.311459 0.049 Uiso 0.442(14) 1 calc R U P A 2
C6B C 0.552(3) 0.8291(7) 0.4646(10) 0.039(2) Uani 0.442(14) 1 d DG U P A 2
C7B C 0.694(4) 0.7556(11) 0.5223(8) 0.041(2) Uani 0.442(14) 1 d G U P A 2
H7B H 0.783591 0.798265 0.599522 0.05 Uiso 0.442(14) 1 calc R U P A 2
C8B C 0.702(4) 0.6189(11) 0.4657(11) 0.041(2) Uani 0.442(14) 1 d G U P A 2
H8B H 0.798198 0.569208 0.504668 0.049 Uiso 0.442(14) 1 calc R U P A 2
N2B N 0.547(3) 0.9698(12) 0.5291(10) 0.043(2) Uani 0.442(14) 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 2.102(4) . ?
I1 N1B 2.929(9) . ?
I1 N1A 2.943(7) . ?
Cl1 C2 1.721(4) . ?
Cl2 C3 1.731(4) . ?
C1 C3 1.396(6) 2_755 ?
C1 C2 1.399(6) . ?
C2 C3 1.390(6) . ?
N1A C4A 1.39 . ?
N1A C8A 1.39 . ?
C4A C5A 1.39 . ?
C4A H4A 0.94 . ?
C5A C6A 1.39 . ?
C5A H5A 0.94 . ?
C6A C7A 1.39 . ?
C6A N2A 1.442(9) . ?
C7A C8A 1.39 . ?
C7A H7A 0.94 . ?
C8A H8A 0.94 . ?
N2A N2A 1.222(19) 2_676 ?
N1B C4B 1.39 . ?
N1B C8B 1.39 . ?
C4B C5B 1.39 . ?
C4B H4B 0.94 . ?
C5B C6B 1.39 . ?
C5B H5B 0.94 . ?
C6B C7B 1.39 . ?
C6B N2B 1.440(12) . ?
C7B C8B 1.39 . ?
C7B H7B 0.94 . ?
C8B H8B 0.94 . ?
N2B N2B 1.20(2) 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
C1 I1 N1B 170.3(3) . . ?
C1 I1 N1A 173.2(3) . . ?
C3 C1 C2 118.2(4) 2_755 . ?
C3 C1 I1 121.0(3) 2_755 . ?
C2 C1 I1 120.9(3) . . ?
C3 C2 C1 120.6(4) . . ?
C3 C2 Cl1 119.4(3) . . ?
C1 C2 Cl1 120.0(3) . . ?
C2 C3 C1 121.2(4) . 2_755 ?
C2 C3 Cl2 118.9(3) . . ?
C1 C3 Cl2 119.9(3) 2_755 . ?
C4A N1A C8A 120 . . ?
C4A N1A I1 99.9(5) . . ?
C8A N1A I1 137.5(5) . . ?
N1A C4A C5A 120 . . ?
N1A C4A H4A 120 . . ?
C5A C4A H4A 120 . . ?
C6A C5A C4A 120 . . ?
C6A C5A H5A 120 . . ?
C4A C5A H5A 120 . . ?
C7A C6A C5A 120 . . ?
C7A C6A N2A 122.9(7) . . ?
C5A C6A N2A 117.1(7) . . ?
C8A C7A C6A 120 . . ?
C8A C7A H7A 120 . . ?
C6A C7A H7A 120 . . ?
C7A C8A N1A 120 . . ?
C7A C8A H8A 120 . . ?
N1A C8A H8A 120 . . ?
N2A N2A C6A 114.2(11) 2_676 . ?
C4B N1B C8B 120 . . ?
C4B N1B I1 117.7(7) . . ?
C8B N1B I1 119.4(6) . . ?
C5B C4B N1B 120 . . ?
C5B C4B H4B 120 . . ?
N1B C4B H4B 120 . . ?
C4B C5B C6B 120 . . ?
C4B C5B H5B 120 . . ?
C6B C5B H5B 120 . . ?
C7B C6B C5B 120 . . ?
C7B C6B N2B 117.0(9) . . ?
C5B C6B N2B 123.0(9) . . ?
C6B C7B C8B 120 . . ?
C6B C7B H7B 120 . . ?
C8B C7B H7B 120 . . ?
C7B C8B N1B 120 . . ?
C7B C8B H8B 120 . . ?
N1B C8B H8B 120 . . ?
N2B N2B C6B 113.7(15) 2_676 . ?

####################################################################### 
# 
# 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_hut19_48_210
_database_code_depnum_ccdc_archive 'CCDC 1954973'
loop_
_audit_author_name
_audit_author_address
'Daniel K. Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-09-20 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT250_hut19_48_210        
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.7 Note  
RESPONSE: Due to the pedal motion of molecules within the structure.
;
_vrf_PLAT431_hut19_48_210        
;
PROBLEM: Short Inter HL..A Contact  Cl1      ..N2B      .       3.12 Ang.  
RESPONSE: A feature of the structure.
;
_vrf_PLAT911_hut19_48_210        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          7 Report
RESPONSE: ...
;
# end Validation Reply Form


_audit_creation_date             2019-09-05T11:48:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C16 H8 Cl4 I2 N4'
_chemical_formula_weight         651.86

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.02352(16)
_cell_length_b                   10.8276(3)
_cell_length_c                   12.3666(4)
_cell_angle_alpha                111.499(3)
_cell_angle_beta                 92.051(3)
_cell_angle_gamma                94.643(3)
_cell_volume                     498.38(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    9944
_cell_measurement_theta_min      4.354
_cell_measurement_theta_max      77.239

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.054
_exptl_crystal_density_diffrn    2.172
_exptl_crystal_F_000             306
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 6 1 0.0747
1 3 5 0.062
2 4 2 0.0644
0 1 -8 0.0283
0 -5 7 0.0339
0 4 -8 0.0132
0 7 -3 0.0515
-3 0 -1 0.0276
0 -4 8 0.0381
0 -6 -1 0.0462
3 0 1 0.0594
2 3 -2 0.0542


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    29.796
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
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_correction_T_min  0.068
_exptl_absorpt_correction_T_max  0.473
_shelx_estimated_absorpt_T_min   0.1
_shelx_estimated_absorpt_T_max   0.296

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      210(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.1511926
_diffrn_orient_matrix_ub_12      0.1446434
_diffrn_orient_matrix_ub_13      0.0679137
_diffrn_orient_matrix_ub_21      0.0581746
_diffrn_orient_matrix_ub_22      0.018625
_diffrn_orient_matrix_ub_23      -0.1157755
_diffrn_orient_matrix_ub_31      -0.3493801
_diffrn_orient_matrix_ub_32      0.0485562
_diffrn_orient_matrix_ub_33      -0.0003308
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_number            16416
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.851
_diffrn_reflns_theta_max         77.386
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.954
_reflns_Friedel_coverage         0
_reflns_number_total             2012
_reflns_number_gt                1928
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0478P)²+0.7608P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2012
_refine_ls_number_parameters     159
_refine_ls_number_restraints     343
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0798
_refine_ls_wR_factor_gt          0.0762
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.881
_refine_diff_density_min         -1.171
_refine_diff_density_rms         0.162

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 The 4,4'-azopyridine molecule is undergoing detectable pedal motion at
 this temperature. The major and minor positions of the disorder (A and B sites)  
 were allowed to refine their occupancies to a total value of 1. The A and B
 sites had occupancies of 0.58 and 0.42, respectively. To help model this 
 disorder and maintain reasonable ADP values SIMU, RIGU, DFIX and AFIX 
 restraints and constraints were applied. During the final refinements the 
 inconsistent reflections 3 -9 9, -4 -5 8, 4 -8 6, -3 10 1, and -1 -5 14 were
 omitted. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.77181(6) 0.29495(2) 0.21024(2) 0.03408(12) Uani 1 1 d . . . . .
Cl1 Cl 0.7152(3) -0.00737(10) 0.22824(9) 0.0400(2) Uani 1 1 d . . . . .
Cl2 Cl 0.9177(3) -0.26508(10) 0.04557(9) 0.0430(3) Uani 1 1 d . . . . .
C1 C 0.9080(10) 0.1182(4) 0.0844(3) 0.0294(8) Uani 1 1 d . . . . .
C2 C 0.8746(10) -0.0020(4) 0.1023(3) 0.0307(8) Uani 1 1 d . . . . .
C3 C 0.9642(11) -0.1188(4) 0.0190(3) 0.0300(8) Uani 1 1 d . . . . .
N1A N 0.600(3) 0.5571(5) 0.3663(8) 0.0366(16) Uani 0.579(14) 1 d G U P A 1
C4A C 0.440(3) 0.5993(7) 0.2864(6) 0.0371(16) Uani 0.579(14) 1 d G U P A 1
H4A H 0.36657 0.537468 0.211702 0.045 Uiso 0.579(14) 1 calc R U P A 1
C5A C 0.389(2) 0.7330(8) 0.3168(7) 0.0362(17) Uani 0.579(14) 1 d G U P A 1
H5A H 0.281416 0.761527 0.262774 0.043 Uiso 0.579(14) 1 calc R U P A 1
C6A C 0.498(2) 0.8244(5) 0.4272(8) 0.0334(16) Uani 0.579(14) 1 d DG U P A 1
C7A C 0.658(3) 0.7822(7) 0.5072(6) 0.0351(18) Uani 0.579(14) 1 d G U P A 1
H7A H 0.731184 0.843985 0.581846 0.042 Uiso 0.579(14) 1 calc R U P A 1
C8A C 0.708(3) 0.6485(8) 0.4767(7) 0.0383(17) Uani 0.579(14) 1 d G U P A 1
H8A H 0.816341 0.619926 0.530776 0.046 Uiso 0.579(14) 1 calc R U P A 1
N2A N 0.444(2) 0.9617(8) 0.4518(7) 0.0377(17) Uani 0.579(14) 1 d D U P A 1
N1B N 0.575(5) 0.5559(8) 0.3518(12) 0.042(2) Uani 0.421(14) 1 d G U P A 2
C4B C 0.430(4) 0.6290(12) 0.2942(9) 0.042(2) Uani 0.421(14) 1 d G U P A 2
H4B H 0.339308 0.586141 0.216954 0.051 Uiso 0.421(14) 1 calc R U P A 2
C5B C 0.418(4) 0.7655(11) 0.3509(10) 0.037(2) Uani 0.421(14) 1 d G U P A 2
H5B H 0.320477 0.814988 0.311954 0.045 Uiso 0.421(14) 1 calc R U P A 2
C6B C 0.552(3) 0.8290(7) 0.4652(10) 0.035(2) Uani 0.421(14) 1 d DG U P A 2
C7B C 0.697(4) 0.7559(11) 0.5227(8) 0.038(2) Uani 0.421(14) 1 d G U P A 2
H7B H 0.787571 0.798735 0.600011 0.046 Uiso 0.421(14) 1 calc R U P A 2
C8B C 0.708(4) 0.6193(11) 0.4661(12) 0.038(2) Uani 0.421(14) 1 d G U P A 2
H8B H 0.806405 0.569887 0.505012 0.046 Uiso 0.421(14) 1 calc R U P A 2
N2B N 0.551(3) 0.9703(12) 0.5291(9) 0.038(2) Uani 0.421(14) 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 2.106(4) . ?
I1 N1B 2.918(9) . ?
I1 N1A 2.942(6) . ?
Cl1 C2 1.724(4) . ?
Cl2 C3 1.730(4) . ?
C1 C2 1.394(6) . ?
C1 C3 1.396(6) 2_755 ?
C2 C3 1.392(6) . ?
N1A C4A 1.39 . ?
N1A C8A 1.39 . ?
C4A C5A 1.39 . ?
C4A H4A 0.94 . ?
C5A C6A 1.39 . ?
C5A H5A 0.94 . ?
C6A C7A 1.39 . ?
C6A N2A 1.440(9) . ?
C7A C8A 1.39 . ?
C7A H7A 0.94 . ?
C8A H8A 0.94 . ?
N2A N2A 1.219(18) 2_676 ?
N1B C4B 1.39 . ?
N1B C8B 1.39 . ?
C4B C5B 1.39 . ?
C4B H4B 0.94 . ?
C5B C6B 1.39 . ?
C5B H5B 0.94 . ?
C6B C7B 1.39 . ?
C6B N2B 1.443(12) . ?
C7B C8B 1.39 . ?
C7B H7B 0.94 . ?
C8B H8B 0.94 . ?
N2B N2B 1.21(2) 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
C1 I1 N1B 170.2(3) . . ?
C1 I1 N1A 173.2(2) . . ?
C2 C1 C3 118.4(4) . 2_755 ?
C2 C1 I1 120.9(3) . . ?
C3 C1 I1 120.6(3) 2_755 . ?
C3 C2 C1 120.9(4) . . ?
C3 C2 Cl1 119.2(3) . . ?
C1 C2 Cl1 119.9(3) . . ?
C2 C3 C1 120.7(4) . 2_755 ?
C2 C3 Cl2 119.0(3) . . ?
C1 C3 Cl2 120.3(3) 2_755 . ?
C4A N1A C8A 120 . . ?
C4A N1A I1 100.3(4) . . ?
C8A N1A I1 136.8(4) . . ?
C5A C4A N1A 120 . . ?
C5A C4A H4A 120 . . ?
N1A C4A H4A 120 . . ?
C4A C5A C6A 120 . . ?
C4A C5A H5A 120 . . ?
C6A C5A H5A 120 . . ?
C7A C6A C5A 120 . . ?
C7A C6A N2A 123.0(6) . . ?
C5A C6A N2A 117.0(6) . . ?
C8A C7A C6A 120 . . ?
C8A C7A H7A 120 . . ?
C6A C7A H7A 120 . . ?
C7A C8A N1A 120 . . ?
C7A C8A H8A 120 . . ?
N1A C8A H8A 120 . . ?
N2A N2A C6A 114.3(10) 2_676 . ?
C4B N1B C8B 120 . . ?
C4B N1B I1 117.7(6) . . ?
C8B N1B I1 119.7(6) . . ?
N1B C4B C5B 120 . . ?
N1B C4B H4B 120 . . ?
C5B C4B H4B 120 . . ?
C6B C5B C4B 120 . . ?
C6B C5B H5B 120 . . ?
C4B C5B H5B 120 . . ?
C5B C6B C7B 120 . . ?
C5B C6B N2B 123.0(9) . . ?
C7B C6B N2B 117.0(9) . . ?
C6B C7B C8B 120 . . ?
C6B C7B H7B 120 . . ?
C8B C7B H7B 120 . . ?
C7B C8B N1B 120 . . ?
C7B C8B H8B 120 . . ?
N1B C8B H8B 120 . . ?
N2B N2B C6B 113.5(14) 2_676 . ?

####################################################################### 
# 
# 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_hut19_48_190
_database_code_depnum_ccdc_archive 'CCDC 1954972'
loop_
_audit_author_name
_audit_author_address
'Daniel K. Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-09-20 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT250_hut19_48_190        
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.7 Note  
RESPONSE: Due to the pedal motion of molecules within the structure.
;
_vrf_PLAT431_hut19_48_190        
;
PROBLEM: Short Inter HL..A Contact  Cl1      ..N2B      .       3.11 Ang.  
RESPONSE: A feature of the structure.
;
_vrf_PLAT911_hut19_48_190        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          7 Report
RESPONSE: ...
;
# end Validation Reply Form


_audit_creation_date             2019-09-05T11:46:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C16 H8 Cl4 I2 N4'
_chemical_formula_weight         651.86

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.01450(14)
_cell_length_b                   10.8241(2)
_cell_length_c                   12.3534(3)
_cell_angle_alpha                111.476(2)
_cell_angle_beta                 92.043(3)
_cell_angle_gamma                94.580(2)
_cell_volume                     496.72(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    10195
_cell_measurement_theta_min      3.894
_cell_measurement_theta_max      77.131

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.054
_exptl_crystal_density_diffrn    2.179
_exptl_crystal_F_000             306
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 6 1 0.0747
-3 0 -1 0.0276
0 -6 -1 0.0462
3 0 1 0.0594
2 4 2 0.0644
0 4 -8 0.0132
0 -4 8 0.0381
0 7 -3 0.0515
2 3 -2 0.0542
1 3 5 0.062
0 -5 7 0.0339
0 1 -8 0.0283


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    29.895
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.58a (Rigaku Oxford Diffraction, 2019)
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_correction_T_min  0.067
_exptl_absorpt_correction_T_max  0.475
_shelx_estimated_absorpt_T_min   0.1
_shelx_estimated_absorpt_T_max   0.295

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      190(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.1497906
_diffrn_orient_matrix_ub_12      0.1444586
_diffrn_orient_matrix_ub_13      0.0694391
_diffrn_orient_matrix_ub_21      0.0569472
_diffrn_orient_matrix_ub_22      0.02099
_diffrn_orient_matrix_ub_23      -0.1150005
_diffrn_orient_matrix_ub_31      -0.3510809
_diffrn_orient_matrix_ub_32      0.0481571
_diffrn_orient_matrix_ub_33      0.0006419
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_number            16568
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.855
_diffrn_reflns_theta_max         77.275
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.957
_reflns_Friedel_coverage         0
_reflns_number_total             2008
_reflns_number_gt                1934
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0528P)²+0.8008P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2008
_refine_ls_number_parameters     159
_refine_ls_number_restraints     343
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0846
_refine_ls_wR_factor_gt          0.0816
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.032
_refine_diff_density_min         -1.157
_refine_diff_density_rms         0.17

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 The 4,4'-azopyridine molecule is undergoing detectable pedal motion at
 this temperature. The major and minor positions of the disorder (A and B sites)  
 were allowed to refine their occupancies to a total value of 1. The A and B
 sites had occupancies of 0.60 and 0.40, respectively. To help model this 
 disorder and maintain reasonable ADP values SIMU, RIGU, DFIX and AFIX 
 restraints and constraints were applied. During the final refinements the 
 inconsistent reflections 3 -9 9, 2 9 3, 0 12 0, -3 -2 12, -4 -5 8, -4 5 0, 
 -3 10 1, and 1 -13 3 were omitted. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.77150(6) 0.29489(2) 0.21081(2) 0.03133(13) Uani 1 1 d . . . . .
Cl1 Cl 0.7139(3) -0.00780(11) 0.22845(9) 0.0368(3) Uani 1 1 d . . . . .
Cl2 Cl 0.9162(3) -0.26553(10) 0.04504(10) 0.0394(3) Uani 1 1 d . . . . .
C1 C 0.9082(10) 0.1185(4) 0.0850(3) 0.0272(8) Uani 1 1 d . . . . .
C2 C 0.8742(11) -0.0025(4) 0.1026(3) 0.0280(8) Uani 1 1 d . . . . .
C3 C 0.9621(11) -0.1186(4) 0.0190(4) 0.0286(8) Uani 1 1 d . . . . .
N1A N 0.600(3) 0.5565(5) 0.3655(8) 0.0339(16) Uani 0.601(14) 1 d G U P A 1
C4A C 0.438(3) 0.5989(7) 0.2859(6) 0.0339(16) Uani 0.601(14) 1 d G U P A 1
H4A H 0.363111 0.536536 0.210397 0.041 Uiso 0.601(14) 1 calc R U P A 1
C5A C 0.386(2) 0.7326(8) 0.3166(7) 0.0323(16) Uani 0.601(14) 1 d G U P A 1
H5A H 0.275939 0.761565 0.262214 0.039 Uiso 0.601(14) 1 calc R U P A 1
C6A C 0.496(2) 0.8239(5) 0.4271(7) 0.0309(16) Uani 0.601(14) 1 d DG U P A 1
C7A C 0.658(2) 0.7815(6) 0.5067(6) 0.0318(17) Uani 0.601(14) 1 d G U P A 1
H7A H 0.733089 0.843881 0.582161 0.038 Uiso 0.601(14) 1 calc R U P A 1
C8A C 0.710(3) 0.6478(7) 0.4759(7) 0.0346(16) Uani 0.601(14) 1 d G U P A 1
H8A H 0.820264 0.618852 0.530346 0.042 Uiso 0.601(14) 1 calc R U P A 1
N2A N 0.4423(19) 0.9611(8) 0.4512(7) 0.0329(17) Uani 0.601(14) 1 d D U P A 1
N1B N 0.571(5) 0.5551(8) 0.3535(13) 0.038(2) Uani 0.399(14) 1 d G U P A 2
C4B C 0.430(5) 0.6283(12) 0.2949(9) 0.038(2) Uani 0.399(14) 1 d G U P A 2
H4B H 0.338686 0.584742 0.216738 0.046 Uiso 0.399(14) 1 calc R U P A 2
C5B C 0.422(4) 0.7651(12) 0.3508(11) 0.035(2) Uani 0.399(14) 1 d G U P A 2
H5B H 0.325316 0.815122 0.310793 0.042 Uiso 0.399(14) 1 calc R U P A 2
C6B C 0.555(3) 0.8288(8) 0.4652(11) 0.031(2) Uani 0.399(14) 1 d DG U P A 2
C7B C 0.696(4) 0.7557(12) 0.5238(9) 0.035(2) Uani 0.399(14) 1 d G U P A 2
H7B H 0.786677 0.799193 0.601947 0.042 Uiso 0.399(14) 1 calc R U P A 2
C8B C 0.704(5) 0.6188(12) 0.4679(13) 0.036(2) Uani 0.399(14) 1 d G U P A 2
H8B H 0.800049 0.568813 0.507893 0.043 Uiso 0.399(14) 1 calc R U P A 2
N2B N 0.548(3) 0.9701(12) 0.5290(10) 0.036(2) Uani 0.399(14) 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 2.101(4) . ?
I1 N1B 2.919(10) . ?
I1 N1A 2.931(6) . ?
Cl1 C2 1.722(4) . ?
Cl2 C3 1.732(4) . ?
C1 C2 1.401(6) . ?
C1 C3 1.404(6) 2_755 ?
C2 C3 1.384(6) . ?
N1A C4A 1.39 . ?
N1A C8A 1.39 . ?
C4A C5A 1.39 . ?
C4A H4A 0.95 . ?
C5A C6A 1.39 . ?
C5A H5A 0.95 . ?
C6A C7A 1.39 . ?
C6A N2A 1.440(8) . ?
C7A C8A 1.39 . ?
C7A H7A 0.95 . ?
C8A H8A 0.95 . ?
N2A N2A 1.238(16) 2_676 ?
N1B C4B 1.39 . ?
N1B C8B 1.39 . ?
C4B C5B 1.39 . ?
C4B H4B 0.95 . ?
C5B C6B 1.39 . ?
C5B H5B 0.95 . ?
C6B C7B 1.39 . ?
C6B N2B 1.444(13) . ?
C7B C8B 1.39 . ?
C7B H7B 0.95 . ?
C8B H8B 0.95 . ?
N2B N2B 1.20(3) 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
C1 I1 N1B 170.5(3) . . ?
C1 I1 N1A 172.9(2) . . ?
C2 C1 C3 118.0(4) . 2_755 ?
C2 C1 I1 121.1(3) . . ?
C3 C1 I1 120.9(3) 2_755 . ?
C3 C2 C1 120.8(4) . . ?
C3 C2 Cl1 119.5(3) . . ?
C1 C2 Cl1 119.7(3) . . ?
C2 C3 C1 121.2(4) . 2_755 ?
C2 C3 Cl2 119.1(3) . . ?
C1 C3 Cl2 119.7(3) 2_755 . ?
C4A N1A C8A 120 . . ?
C4A N1A I1 100.7(4) . . ?
C8A N1A I1 136.5(4) . . ?
N1A C4A C5A 120 . . ?
N1A C4A H4A 120 . . ?
C5A C4A H4A 120 . . ?
C6A C5A C4A 120 . . ?
C6A C5A H5A 120 . . ?
C4A C5A H5A 120 . . ?
C5A C6A C7A 120 . . ?
C5A C6A N2A 116.7(6) . . ?
C7A C6A N2A 123.3(6) . . ?
C8A C7A C6A 120 . . ?
C8A C7A H7A 120 . . ?
C6A C7A H7A 120 . . ?
C7A C8A N1A 120 . . ?
C7A C8A H8A 120 . . ?
N1A C8A H8A 120 . . ?
N2A N2A C6A 114.0(9) 2_676 . ?
C4B N1B C8B 120 . . ?
C4B N1B I1 117.0(7) . . ?
C8B N1B I1 120.0(7) . . ?
N1B C4B C5B 120 . . ?
N1B C4B H4B 120 . . ?
C5B C4B H4B 120 . . ?
C6B C5B C4B 120 . . ?
C6B C5B H5B 120 . . ?
C4B C5B H5B 120 . . ?
C5B C6B C7B 120 . . ?
C5B C6B N2B 122.7(10) . . ?
C7B C6B N2B 117.3(10) . . ?
C8B C7B C6B 120 . . ?
C8B C7B H7B 120 . . ?
C6B C7B H7B 120 . . ?
C7B C8B N1B 120 . . ?
C7B C8B H8B 120 . . ?
N1B C8B H8B 120 . . ?
N2B N2B C6B 114.2(15) 2_676 . ?

####################################################################### 
# 
# 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_hut19_48_270
_database_code_depnum_ccdc_archive 'CCDC 1954976'
loop_
_audit_author_name
_audit_author_address
'Daniel K. Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-09-20 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT250_hut19_48_270        
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.8 Note  
RESPONSE: Due to the pedal motion of molecules within the structure.
;
_vrf_PLAT431_hut19_48_270        
;
PROBLEM: Short Inter HL..A Contact  Cl1      ..N2B      .       3.14 Ang.  
RESPONSE: A feature of the structure.
;
_vrf_PLAT911_hut19_48_270        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2019-09-05T11:55:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C16 H8 Cl4 I2 N4'
_chemical_formula_weight         651.86

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.05043(19)
_cell_length_b                   10.8317(3)
_cell_length_c                   12.4043(3)
_cell_angle_alpha                111.501(3)
_cell_angle_beta                 92.105(3)
_cell_angle_gamma                94.666(3)
_cell_volume                     503.36(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    9356
_cell_measurement_theta_min      3.864
_cell_measurement_theta_max      76.721

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.054
_exptl_crystal_density_diffrn    2.15
_exptl_crystal_F_000             306
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 6 1 0.0747
2 3 -2 0.0542
3 0 1 0.0594
0 -6 -1 0.0462
0 -4 8 0.0381
-3 0 -1 0.0276
0 7 -3 0.0515
0 4 -8 0.0132
1 3 5 0.062
0 -5 7 0.0339
0 1 -8 0.0283
2 4 2 0.0644


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    29.501
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.58a (Rigaku Oxford Diffraction, 2019)
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_correction_T_min  0.068
_exptl_absorpt_correction_T_max  0.472
_shelx_estimated_absorpt_T_min   0.101
_shelx_estimated_absorpt_T_max   0.299

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      270(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.1498978
_diffrn_orient_matrix_ub_12      0.1446448
_diffrn_orient_matrix_ub_13      0.0679473
_diffrn_orient_matrix_ub_21      0.0578681
_diffrn_orient_matrix_ub_22      0.0188751
_diffrn_orient_matrix_ub_23      -0.1152971
_diffrn_orient_matrix_ub_31      -0.3472209
_diffrn_orient_matrix_ub_32      0.0483221
_diffrn_orient_matrix_ub_33      -0.000466
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_number            16741
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.84
_diffrn_reflns_theta_max         77.395
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.956
_reflns_Friedel_coverage         0
_reflns_number_total             2041
_reflns_number_gt                1915
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0488P)²+0.9372P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2041
_refine_ls_number_parameters     159
_refine_ls_number_restraints     343
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0911
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.832
_refine_diff_density_min         -1.11
_refine_diff_density_rms         0.154

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 The 4,4'-azopyridine molecule is undergoing detectable pedal motion at
 this temperature. The major and minor positions of the disorder (A and B sites)  
 were allowed to refine their occupancies to a total value of 1. The A and B
 sites had occupancies of 0.54 and 0.46, respectively. To help model this 
 disorder and maintain reasonable ADP values SIMU, RIGU, DFIX and AFIX 
 restraints and constraints were applied. During the final refinements the 
 inconsistent reflections 3 -9 9, 2 9 3, and 0 12 0 were omitted. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.77275(7) 0.29479(3) 0.20903(2) 0.04408(14) Uani 1 1 d . . . . .
Cl1 Cl 0.7191(4) -0.00688(13) 0.22783(10) 0.0521(3) Uani 1 1 d . . . . .
Cl2 Cl 0.9213(4) -0.26434(12) 0.04625(12) 0.0556(3) Uani 1 1 d . . . . .
C1 C 0.9079(11) 0.1182(4) 0.0838(4) 0.0360(9) Uani 1 1 d . . . . .
C2 C 0.8761(12) -0.0018(5) 0.1020(4) 0.0387(10) Uani 1 1 d . . . . .
C3 C 0.9669(13) -0.1182(5) 0.0192(4) 0.0400(10) Uani 1 1 d . . . . .
N1A N 0.612(4) 0.5581(6) 0.3670(9) 0.0468(19) Uani 0.542(15) 1 d G U P A 1
C4A C 0.450(3) 0.5993(8) 0.2872(7) 0.0464(19) Uani 0.542(15) 1 d G U P A 1
H4A H 0.378977 0.537812 0.213545 0.056 Uiso 0.542(15) 1 calc R U P A 1
C5A C 0.395(3) 0.7325(10) 0.3174(8) 0.046(2) Uani 0.542(15) 1 d G U P A 1
H5A H 0.287415 0.760064 0.26402 0.055 Uiso 0.542(15) 1 calc R U P A 1
C6A C 0.502(3) 0.8244(6) 0.4275(9) 0.0450(18) Uani 0.542(15) 1 d DG U P A 1
C7A C 0.664(3) 0.7831(8) 0.5073(7) 0.044(2) Uani 0.542(15) 1 d G U P A 1
H7A H 0.734868 0.844636 0.58097 0.053 Uiso 0.542(15) 1 calc R U P A 1
C8A C 0.718(3) 0.6500(9) 0.4771(8) 0.049(2) Uani 0.542(15) 1 d G U P A 1
H8A H 0.826433 0.622385 0.530497 0.059 Uiso 0.542(15) 1 calc R U P A 1
N2A N 0.447(2) 0.9610(10) 0.4510(9) 0.046(2) Uani 0.542(15) 1 d D U P A 1
N1B N 0.567(4) 0.5558(7) 0.3513(11) 0.052(2) Uani 0.458(15) 1 d G U P A 2
C4B C 0.425(4) 0.6298(12) 0.2944(8) 0.053(2) Uani 0.458(15) 1 d G U P A 2
H4B H 0.334711 0.587913 0.21824 0.063 Uiso 0.458(15) 1 calc R U P A 2
C5B C 0.417(4) 0.7664(11) 0.3514(11) 0.047(2) Uani 0.458(15) 1 d G U P A 2
H5B H 0.32201 0.815909 0.313299 0.057 Uiso 0.458(15) 1 calc R U P A 2
C6B C 0.552(4) 0.8290(7) 0.4652(10) 0.045(2) Uani 0.458(15) 1 d DG U P A 2
C7B C 0.694(4) 0.7550(11) 0.5221(8) 0.048(2) Uani 0.458(15) 1 d G U P A 2
H7B H 0.783776 0.796825 0.598248 0.057 Uiso 0.458(15) 1 calc R U P A 2
C8B C 0.701(4) 0.6184(11) 0.4651(11) 0.047(2) Uani 0.458(15) 1 d G U P A 2
H8B H 0.796479 0.568828 0.503191 0.057 Uiso 0.458(15) 1 calc R U P A 2
N2B N 0.548(3) 0.9707(11) 0.5291(10) 0.048(2) Uani 0.458(15) 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 2.103(4) . ?
I1 N1B 2.939(9) . ?
I1 N1A 2.949(7) . ?
Cl1 C2 1.725(5) . ?
Cl2 C3 1.732(5) . ?
C1 C3 1.392(7) 2_755 ?
C1 C2 1.396(7) . ?
C2 C3 1.391(7) . ?
N1A C4A 1.39 . ?
N1A C8A 1.39 . ?
C4A C5A 1.39 . ?
C4A H4A 0.93 . ?
C5A C6A 1.39 . ?
C5A H5A 0.93 . ?
C6A C7A 1.39 . ?
C6A N2A 1.438(10) . ?
C7A C8A 1.39 . ?
C7A H7A 0.93 . ?
C8A H8A 0.93 . ?
N2A N2A 1.24(2) 2_676 ?
N1B C4B 1.39 . ?
N1B C8B 1.39 . ?
C4B C5B 1.39 . ?
C4B H4B 0.93 . ?
C5B C6B 1.39 . ?
C5B H5B 0.93 . ?
C6B C7B 1.39 . ?
C6B N2B 1.448(12) . ?
C7B C8B 1.39 . ?
C7B H7B 0.93 . ?
C8B H8B 0.93 . ?
N2B N2B 1.20(3) 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
C1 I1 N1B 170.5(3) . . ?
C1 I1 N1A 173.4(3) . . ?
C3 C1 C2 118.2(4) 2_755 . ?
C3 C1 I1 120.8(3) 2_755 . ?
C2 C1 I1 121.0(3) . . ?
C3 C2 C1 120.8(4) . . ?
C3 C2 Cl1 119.4(4) . . ?
C1 C2 Cl1 119.8(4) . . ?
C2 C3 C1 121.0(4) . 2_755 ?
C2 C3 Cl2 118.7(4) . . ?
C1 C3 Cl2 120.2(4) 2_755 . ?
C4A N1A C8A 120 . . ?
C4A N1A I1 99.4(5) . . ?
C8A N1A I1 138.0(5) . . ?
N1A C4A C5A 120 . . ?
N1A C4A H4A 120 . . ?
C5A C4A H4A 120 . . ?
C6A C5A C4A 120 . . ?
C6A C5A H5A 120 . . ?
C4A C5A H5A 120 . . ?
C5A C6A C7A 120 . . ?
C5A C6A N2A 116.8(7) . . ?
C7A C6A N2A 123.2(7) . . ?
C8A C7A C6A 120 . . ?
C8A C7A H7A 120 . . ?
C6A C7A H7A 120 . . ?
C7A C8A N1A 120 . . ?
C7A C8A H8A 120 . . ?
N1A C8A H8A 120 . . ?
N2A N2A C6A 114.1(12) 2_676 . ?
C4B N1B C8B 120 . . ?
C4B N1B I1 118.0(7) . . ?
C8B N1B I1 119.0(6) . . ?
C5B C4B N1B 120 . . ?
C5B C4B H4B 120 . . ?
N1B C4B H4B 120 . . ?
C4B C5B C6B 120 . . ?
C4B C5B H5B 120 . . ?
C6B C5B H5B 120 . . ?
C7B C6B C5B 120 . . ?
C7B C6B N2B 117.6(9) . . ?
C5B C6B N2B 122.4(9) . . ?
C6B C7B C8B 120 . . ?
C6B C7B H7B 120 . . ?
C8B C7B H7B 120 . . ?
C7B C8B N1B 120 . . ?
C7B C8B H8B 120 . . ?
N1B C8B H8B 120 . . ?
N2B N2B C6B 113.5(15) 2_676 . ?

####################################################################### 
# 
# 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_hut19_48_290
_database_code_depnum_ccdc_archive 'CCDC 1954977'
loop_
_audit_author_name
_audit_author_address
'Daniel K. Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-09-20 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_hut19_48_290        
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.960 Why?  
RESPONSE: Due to the loss of high angle diffraction peaks at this temperature.
;
_vrf_PLAT342_hut19_48_290        
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00867 Ang.  
RESPONSE: A result of the loss of high angle diffraction peaks.
;
_vrf_PLAT250_hut19_48_290        
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.6 Note  
RESPONSE: Due to the pedal motion of molecules within the structure.
;
_vrf_PLAT431_hut19_48_290        
;
PROBLEM: Short Inter HL..A Contact  Cl1      ..N2B      .       3.14 Ang.  
RESPONSE: A feature of the structure.
;
_vrf_PLAT911_hut19_48_290        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          73 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2019-09-05T11:56:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C16 H8 Cl4 I2 N4'
_chemical_formula_weight         651.86

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.05852(19)
_cell_length_b                   10.8342(4)
_cell_length_c                   12.4194(4)
_cell_angle_alpha                111.498(3)
_cell_angle_beta                 92.143(3)
_cell_angle_gamma                94.631(3)
_cell_volume                     505.12(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    8639
_cell_measurement_theta_min      3.889
_cell_measurement_theta_max      77.195

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.054
_exptl_crystal_density_diffrn    2.143
_exptl_crystal_F_000             306
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 6 1 0.0747
2 3 -2 0.0542
3 0 1 0.0594
0 -6 -1 0.0462
0 -4 8 0.0381
-3 0 -1 0.0276
0 7 -4 0.0515
0 4 -8 0.0132
1 4 4 0.062
0 -4 8 0.0339
0 0 -7 0.0283
2 4 1 0.0644


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    29.398
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.58a (Rigaku Oxford Diffraction, 2019)
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_correction_T_min  0.068
_exptl_absorpt_correction_T_max  0.473
_shelx_estimated_absorpt_T_min   0.102
_shelx_estimated_absorpt_T_max   0.3

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      290(2)
_diffrn_ambient_environment      air
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.1488655
_diffrn_orient_matrix_ub_12      0.1456918
_diffrn_orient_matrix_ub_13      0.0630197
_diffrn_orient_matrix_ub_21      0.053818
_diffrn_orient_matrix_ub_22      0.0124018
_diffrn_orient_matrix_ub_23      -0.1178943
_diffrn_orient_matrix_ub_31      -0.3474752
_diffrn_orient_matrix_ub_32      0.0471833
_diffrn_orient_matrix_ub_33      -0.0018571
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0854
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_number            13253
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.835
_diffrn_reflns_theta_max         76.485
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.96
_diffrn_measured_fraction_theta_max 0.891
_diffrn_reflns_Laue_measured_fraction_full 0.96
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_point_group_measured_fraction_full 0.96
_diffrn_reflns_point_group_measured_fraction_max 0.891
_reflns_Friedel_coverage         0
_reflns_number_total             1883
_reflns_number_gt                1759
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²+1.4244P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1883
_refine_ls_number_parameters     159
_refine_ls_number_restraints     343
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0962
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.05
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.744
_refine_diff_density_min         -1.011
_refine_diff_density_rms         0.139

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 The 4,4'-azopyridine molecule is undergoing detectable pedal motion at
 this temperature. The major and minor positions of the disorder (A and B sites)  
 were allowed to refine their occupancies to a total value of 1. The A and B
 sites had occupancies of 0.55 and 0.46, respectively. To help model this 
 disorder and maintain reasonable ADP values SIMU, RIGU, DFIX and AFIX 
 restraints and constraints were applied. During the final refinements the 
 inconsistent reflections -3 8 3, 4 -3 6, -1 -9 12 and 0 12 0 were omitted. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.77300(9) 0.29471(3) 0.20867(3) 0.04812(17) Uani 1 1 d . . . . .
Cl1 Cl 0.7202(5) -0.00661(16) 0.22777(13) 0.0572(4) Uani 1 1 d . . . . .
Cl2 Cl 0.9231(5) -0.26421(15) 0.04620(14) 0.0602(4) Uani 1 1 d . . . . .
C1 C 0.9087(14) 0.1178(5) 0.0837(5) 0.0410(12) Uani 1 1 d . . . . .
C2 C 0.8750(14) -0.0018(6) 0.1019(5) 0.0401(12) Uani 1 1 d . . . . .
C3 C 0.9687(15) -0.1186(5) 0.0192(5) 0.0415(12) Uani 1 1 d . . . . .
N1A N 0.598(5) 0.5576(7) 0.3678(11) 0.052(2) Uani 0.547(17) 1 d G U P A 1
C4A C 0.441(4) 0.6005(10) 0.2884(8) 0.053(2) Uani 0.547(17) 1 d G U P A 1
H4A H 0.366506 0.53959 0.214901 0.064 Uiso 0.547(17) 1 calc R U P A 1
C5A C 0.395(4) 0.7345(11) 0.3187(9) 0.053(2) Uani 0.547(17) 1 d G U P A 1
H5A H 0.289771 0.763227 0.265601 0.063 Uiso 0.547(17) 1 calc R U P A 1
C6A C 0.506(4) 0.8256(7) 0.4285(10) 0.049(2) Uani 0.547(17) 1 d DG U P A 1
C7A C 0.663(4) 0.7827(9) 0.5079(8) 0.051(2) Uani 0.547(17) 1 d G U P A 1
H7A H 0.737507 0.843625 0.581361 0.061 Uiso 0.547(17) 1 calc R U P A 1
C8A C 0.709(4) 0.6487(11) 0.4775(10) 0.054(2) Uani 0.547(17) 1 d G U P A 1
H8A H 0.814243 0.619987 0.530663 0.064 Uiso 0.547(17) 1 calc R U P A 1
N2A N 0.446(3) 0.9622(11) 0.4526(11) 0.051(2) Uani 0.547(17) 1 d D U P A 1
N1B N 0.585(6) 0.5568(9) 0.3499(13) 0.056(2) Uani 0.453(17) 1 d G U P A 2
C4B C 0.439(5) 0.6301(13) 0.2931(10) 0.057(3) Uani 0.453(17) 1 d G U P A 2
H4B H 0.354111 0.588322 0.216416 0.068 Uiso 0.453(17) 1 calc R U P A 2
C5B C 0.421(4) 0.7659(13) 0.3509(12) 0.053(2) Uani 0.453(17) 1 d G U P A 2
H5B H 0.323369 0.814913 0.312857 0.063 Uiso 0.453(17) 1 calc R U P A 2
C6B C 0.548(4) 0.8283(8) 0.4655(12) 0.050(2) Uani 0.453(17) 1 d DG U P A 2
C7B C 0.693(5) 0.7550(13) 0.5223(9) 0.052(2) Uani 0.453(17) 1 d G U P A 2
H7B H 0.778133 0.796836 0.598948 0.062 Uiso 0.453(17) 1 calc R U P A 2
C8B C 0.712(5) 0.6193(13) 0.4645(13) 0.051(2) Uani 0.453(17) 1 d G U P A 2
H8B H 0.808878 0.570244 0.502509 0.062 Uiso 0.453(17) 1 calc R U P A 2
N2B N 0.549(4) 0.9691(13) 0.5299(12) 0.050(3) Uani 0.453(17) 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 2.107(5) . ?
I1 N1B 2.920(10) . ?
I1 N1A 2.971(9) . ?
Cl1 C2 1.723(6) . ?
Cl2 C3 1.727(6) . ?
C1 C3 1.391(8) 2_755 ?
C1 C2 1.392(8) . ?
C2 C3 1.399(8) . ?
N1A C4A 1.39 . ?
N1A C8A 1.39 . ?
C4A C5A 1.39 . ?
C4A H4A 0.93 . ?
C5A C6A 1.39 . ?
C5A H5A 0.93 . ?
C6A C7A 1.39 . ?
C6A N2A 1.441(11) . ?
C7A C8A 1.39 . ?
C7A H7A 0.93 . ?
C8A H8A 0.93 . ?
N2A N2A 1.20(3) 2_676 ?
N1B C4B 1.39 . ?
N1B C8B 1.39 . ?
C4B C5B 1.39 . ?
C4B H4B 0.93 . ?
C5B C6B 1.39 . ?
C5B H5B 0.93 . ?
C6B C7B 1.39 . ?
C6B N2B 1.439(13) . ?
C7B C8B 1.39 . ?
C7B H7B 0.93 . ?
C8B H8B 0.93 . ?
N2B N2B 1.24(3) 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
C1 I1 N1B 170.3(4) . . ?
C1 I1 N1A 174.1(3) . . ?
C3 C1 C2 118.8(5) 2_755 . ?
C3 C1 I1 120.4(4) 2_755 . ?
C2 C1 I1 120.8(4) . . ?
C1 C2 C3 120.6(5) . . ?
C1 C2 Cl1 120.0(4) . . ?
C3 C2 Cl1 119.4(4) . . ?
C1 C3 C2 120.6(5) 2_755 . ?
C1 C3 Cl2 120.7(4) 2_755 . ?
C2 C3 Cl2 118.7(4) . . ?
C4A N1A C8A 120 . . ?
C4A N1A I1 100.0(6) . . ?
C8A N1A I1 136.6(6) . . ?
C5A C4A N1A 120 . . ?
C5A C4A H4A 120 . . ?
N1A C4A H4A 120 . . ?
C4A C5A C6A 120 . . ?
C4A C5A H5A 120 . . ?
C6A C5A H5A 120 . . ?
C7A C6A C5A 120 . . ?
C7A C6A N2A 123.8(8) . . ?
C5A C6A N2A 116.2(8) . . ?
C8A C7A C6A 120 . . ?
C8A C7A H7A 120 . . ?
C6A C7A H7A 120 . . ?
C7A C8A N1A 120 . . ?
C7A C8A H8A 120 . . ?
N1A C8A H8A 120 . . ?
N2A N2A C6A 113.9(14) 2_676 . ?
C4B N1B C8B 120 . . ?
C4B N1B I1 117.8(7) . . ?
C8B N1B I1 120.1(8) . . ?
N1B C4B C5B 120 . . ?
N1B C4B H4B 120 . . ?
C5B C4B H4B 120 . . ?
C4B C5B C6B 120 . . ?
C4B C5B H5B 120 . . ?
C6B C5B H5B 120 . . ?
C7B C6B C5B 120 . . ?
C7B C6B N2B 116.6(11) . . ?
C5B C6B N2B 123.4(11) . . ?
C6B C7B C8B 120 . . ?
C6B C7B H7B 120 . . ?
C8B C7B H7B 120 . . ?
C7B C8B N1B 120 . . ?
C7B C8B H8B 120 . . ?
N1B C8B H8B 120 . . ?
N2B N2B C6B 113.2(16) 2_676 . ?

####################################################################### 
# 
# 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_hut19_49_210
_database_code_depnum_ccdc_archive 'CCDC 1954979'
loop_
_audit_author_name
_audit_author_address
'Daniel K. Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-09-20 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;


_audit_creation_date             2019-09-06T14:44:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H10 Cl4 I2 N2'
_chemical_formula_weight         649.88

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.04426(6)
_cell_length_b                   10.88792(18)
_cell_length_c                   12.30931(18)
_cell_angle_alpha                110.4771(15)
_cell_angle_beta                 92.6533(12)
_cell_angle_gamma                94.5880(13)
_cell_volume                     504.543(15)
_cell_formula_units_Z            1
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    15376
_cell_measurement_theta_min      3.836
_cell_measurement_theta_max      77.133

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.048
_exptl_crystal_density_diffrn    2.139
_exptl_crystal_F_000             306
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -4 7 0.0254
0 7 -3 0.0206
-3 1 -1 0.0667
0 4 -8 0.0449
-3 0 0 0.0713
3 0 0 0.0225
0 -6 -2 0.0356
0 -4 -5 0.0281
0 -6 -1 0.0337
0 6 2 0.0131


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    29.399
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
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_correction_T_min  0.134
_exptl_absorpt_correction_T_max  0.45
_shelx_estimated_absorpt_T_min   0.126
_shelx_estimated_absorpt_T_max   0.333

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      210(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0162502
_diffrn_orient_matrix_ub_12      -0.0136548
_diffrn_orient_matrix_ub_13      -0.1290498
_diffrn_orient_matrix_ub_21      0.0267305
_diffrn_orient_matrix_ub_22      0.1511584
_diffrn_orient_matrix_ub_23      0.0360616
_diffrn_orient_matrix_ub_31      0.382086
_diffrn_orient_matrix_ub_32      0.0045032
_diffrn_orient_matrix_ub_33      0.0026843
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_number            18918
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.845
_diffrn_reflns_theta_max         77.315
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.964
_reflns_Friedel_coverage         0
_reflns_number_total             2062
_reflns_number_gt                2014
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0474P)²+0.1386P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0031(3)
_refine_ls_number_reflns         2062
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0242
_refine_ls_wR_factor_ref         0.0659
_refine_ls_wR_factor_gt          0.0648
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.771
_refine_diff_density_min         -1.034
_refine_diff_density_rms         0.108

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.70925(4) 0.71053(2) 0.28662(2) 0.03049(11) Uani 1 1 d . . . . .
Cl1 Cl 0.4037(2) 0.73350(7) 0.54110(7) 0.0390(2) Uani 1 1 d . . . . .
Cl2 Cl 0.2294(2) 0.98685(7) 0.72846(6) 0.03670(19) Uani 1 1 d . . . . .
N1 N 0.8876(8) 0.4547(3) 0.1435(3) 0.0376(6) Uani 1 1 d . . . . .
C1 C 0.5831(8) 0.8827(3) 0.4136(3) 0.0264(6) Uani 1 1 d . . . . .
C2 C 0.4603(7) 0.8810(3) 0.5169(2) 0.0257(6) Uani 1 1 d . . . . .
C3 C 0.3782(7) 0.9947(3) 0.6016(2) 0.0262(6) Uani 1 1 d . . . . .
C4 C 1.0458(10) 0.4071(3) 0.2154(3) 0.0398(8) Uani 1 1 d . . . . .
H4 H 1.114486 0.465122 0.291287 0.048 Uiso 1 1 calc R U . . .
C5 C 1.1142(9) 0.2783(3) 0.1852(3) 0.0367(7) Uani 1 1 d . . . . .
H5 H 1.230138 0.250614 0.239 0.044 Uiso 1 1 calc R U . . .
C6 C 1.0109(8) 0.1893(3) 0.0745(3) 0.0303(6) Uani 1 1 d . . . . .
C7 C 0.8453(9) 0.2380(3) -0.0010(3) 0.0335(7) Uani 1 1 d . . . . .
H7 H 0.770885 0.181987 -0.077006 0.04 Uiso 1 1 calc R U . . .
C8 C 0.7913(9) 0.3699(3) 0.0372(3) 0.0364(7) Uani 1 1 d . . . . .
H8 H 0.680194 0.401289 -0.015016 0.044 Uiso 1 1 calc R U . . .
C9 C 1.0787(8) 0.0505(3) 0.0435(3) 0.0300(6) Uani 1 1 d . . . . .
H9 H 1.246974 0.032134 0.089115 0.036 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.096(3) . ?
I1 N1 2.896(3) . ?
Cl1 C2 1.732(3) . ?
Cl2 C3 1.726(3) . ?
N1 C8 1.328(4) . ?
N1 C4 1.336(5) . ?
C1 C2 1.391(4) . ?
C1 C3 1.409(4) 2_676 ?
C2 C3 1.388(4) . ?
C4 C5 1.374(5) . ?
C4 H4 0.94 . ?
C5 C6 1.389(5) . ?
C5 H5 0.94 . ?
C6 C7 1.391(4) . ?
C6 C9 1.475(4) . ?
C7 C8 1.386(4) . ?
C7 H7 0.94 . ?
C8 H8 0.94 . ?
C9 C9 1.328(6) 2_755 ?
C9 H9 0.94 . ?

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
C1 I1 N1 170.07(10) . . ?
C8 N1 C4 116.6(3) . . ?
C8 N1 I1 135.2(2) . . ?
C4 N1 I1 106.3(2) . . ?
C2 C1 C3 117.2(3) . 2_676 ?
C2 C1 I1 121.4(2) . . ?
C3 C1 I1 121.4(2) 2_676 . ?
C3 C2 C1 121.7(3) . . ?
C3 C2 Cl1 118.6(2) . . ?
C1 C2 Cl1 119.7(2) . . ?
C2 C3 C1 121.1(3) . 2_676 ?
C2 C3 Cl2 119.7(2) . . ?
C1 C3 Cl2 119.2(2) 2_676 . ?
N1 C4 C5 123.9(3) . . ?
N1 C4 H4 118 . . ?
C5 C4 H4 118 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C7 116.9(3) . . ?
C5 C6 C9 119.2(3) . . ?
C7 C6 C9 123.9(3) . . ?
C8 C7 C6 119.3(3) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
N1 C8 C7 123.8(3) . . ?
N1 C8 H8 118.1 . . ?
C7 C8 H8 118.1 . . ?
C9 C9 C6 125.3(4) 2_755 . ?
C9 C9 H9 117.3 2_755 . ?
C6 C9 H9 117.3 . . ?

####################################################################### 
# 
# 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_hut19_49_190
_database_code_depnum_ccdc_archive 'CCDC 1954978'
loop_
_audit_author_name
_audit_author_address
'Daniel K. Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-09-20 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;

_audit_creation_date             2019-09-06T14:43:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H10 Cl4 I2 N2'
_chemical_formula_weight         649.88

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.03440(10)
_cell_length_b                   10.8835(2)
_cell_length_c                   12.2968(2)
_cell_angle_alpha                110.424(2)
_cell_angle_beta                 92.656(2)
_cell_angle_gamma                94.579(2)
_cell_volume                     502.782(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    15622
_cell_measurement_theta_min      3.823
_cell_measurement_theta_max      77.067

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.048
_exptl_crystal_density_diffrn    2.146
_exptl_crystal_F_000             306
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -4 7 0.0254
0 4 -8 0.0449
-3 1 -1 0.0667
0 6 1 0.0131
0 -6 -2 0.0356
-3 0 0 0.0713
3 0 0 0.0225
0 7 -3 0.0206
0 -4 -5 0.0281
0 -6 -1 0.0337


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    29.502
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
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_correction_T_min  0.133
_exptl_absorpt_correction_T_max  0.448
_shelx_estimated_absorpt_T_min   0.126
_shelx_estimated_absorpt_T_max   0.332

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      190(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0168696
_diffrn_orient_matrix_ub_12      -0.0153204
_diffrn_orient_matrix_ub_13      -0.1295593
_diffrn_orient_matrix_ub_21      0.0271462
_diffrn_orient_matrix_ub_22      0.1510116
_diffrn_orient_matrix_ub_23      0.0345461
_diffrn_orient_matrix_ub_31      0.3829633
_diffrn_orient_matrix_ub_32      0.0042477
_diffrn_orient_matrix_ub_33      0.0025333
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_number            18940
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.848
_diffrn_reflns_theta_max         77.22
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.963
_reflns_Friedel_coverage         0
_reflns_number_total             2051
_reflns_number_gt                1999
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0340P)²+0.4694P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2051
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0578
_refine_ls_wR_factor_gt          0.0565
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.693
_refine_diff_density_min         -0.961
_refine_diff_density_rms         0.111

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 During the final refinements the inconsistent reflections 3 -2 11 and 1 0 1
 were omitted. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.70851(4) 0.71034(2) 0.28631(2) 0.02651(9) Uani 1 1 d . . . . .
Cl1 Cl 0.4016(2) 0.73318(7) 0.54100(7) 0.03423(18) Uani 1 1 d . . . . .
Cl2 Cl 0.2281(2) 0.98678(7) 0.72868(6) 0.03242(17) Uani 1 1 d . . . . .
N1 N 0.8866(8) 0.4552(3) 0.1434(2) 0.0327(6) Uani 1 1 d . . . . .
C1 C 0.5824(7) 0.8828(3) 0.4136(2) 0.0227(6) Uani 1 1 d . . . . .
C2 C 0.4591(7) 0.8806(3) 0.5168(2) 0.0231(6) Uani 1 1 d . . . . .
C3 C 0.3773(7) 0.9947(3) 0.6017(2) 0.0234(6) Uani 1 1 d . . . . .
C4 C 1.0464(9) 0.4075(3) 0.2159(3) 0.0345(7) Uani 1 1 d . . . . .
H4 H 1.115644 0.466209 0.292659 0.041 Uiso 1 1 calc R U . . .
C5 C 1.1156(9) 0.2786(3) 0.1855(3) 0.0312(7) Uani 1 1 d . . . . .
H5 H 1.233924 0.250538 0.239808 0.037 Uiso 1 1 calc R U . . .
C6 C 1.0107(8) 0.1893(3) 0.0743(3) 0.0253(6) Uani 1 1 d . . . . .
C7 C 0.8452(9) 0.2377(3) -0.0011(3) 0.0288(6) Uani 1 1 d . . . . .
H7 H 0.770417 0.181107 -0.078012 0.035 Uiso 1 1 calc R U . . .
C8 C 0.7900(9) 0.3697(3) 0.0370(3) 0.0313(7) Uani 1 1 d . . . . .
H8 H 0.676465 0.401028 -0.015961 0.038 Uiso 1 1 calc R U . . .
C9 C 1.0791(8) 0.0506(3) 0.0435(3) 0.0267(6) Uani 1 1 d . . . . .
H9 H 1.249953 0.032132 0.08964 0.032 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 2.100(3) . ?
I1 N1 2.889(3) . ?
Cl1 C2 1.731(3) . ?
Cl2 C3 1.727(3) . ?
N1 C8 1.332(4) . ?
N1 C4 1.343(5) . ?
C1 C2 1.391(4) . ?
C1 C3 1.408(4) 2_676 ?
C2 C3 1.390(4) . ?
C4 C5 1.376(5) . ?
C4 H4 0.95 . ?
C5 C6 1.395(4) . ?
C5 H5 0.95 . ?
C6 C7 1.387(4) . ?
C6 C9 1.475(4) . ?
C7 C8 1.387(4) . ?
C7 H7 0.95 . ?
C8 H8 0.95 . ?
C9 C9 1.330(6) 2_755 ?
C9 H9 0.95 . ?

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
C1 I1 N1 170.07(10) . . ?
C8 N1 C4 116.4(3) . . ?
C8 N1 I1 135.5(2) . . ?
C4 N1 I1 106.1(2) . . ?
C2 C1 C3 117.5(3) . 2_676 ?
C2 C1 I1 121.3(2) . . ?
C3 C1 I1 121.2(2) 2_676 . ?
C3 C2 C1 121.5(3) . . ?
C3 C2 Cl1 118.7(2) . . ?
C1 C2 Cl1 119.9(2) . . ?
C2 C3 C1 121.1(3) . 2_676 ?
C2 C3 Cl2 119.6(2) . . ?
C1 C3 Cl2 119.3(2) 2_676 . ?
N1 C4 C5 123.8(3) . . ?
N1 C4 H4 118.1 . . ?
C5 C4 H4 118.1 . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C7 C6 C5 117.1(3) . . ?
C7 C6 C9 123.9(3) . . ?
C5 C6 C9 119.0(3) . . ?
C8 C7 C6 119.3(3) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
N1 C8 C7 123.9(3) . . ?
N1 C8 H8 118 . . ?
C7 C8 H8 118 . . ?
C9 C9 C6 125.3(4) 2_755 . ?
C9 C9 H9 117.4 2_755 . ?
C6 C9 H9 117.4 . . ?

####################################################################### 
# 
# 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_hut19_49_250
_database_code_depnum_ccdc_archive 'CCDC 1954981'
loop_
_audit_author_name
_audit_author_address
'Daniel K. Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-09-20 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;

_audit_creation_date             2019-09-06T16:36:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H10 Cl4 I2 N2'
_chemical_formula_weight         649.88

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.06096(6)
_cell_length_b                   10.91085(13)
_cell_length_c                   12.34281(12)
_cell_angle_alpha                110.6602(10)
_cell_angle_beta                 92.5824(10)
_cell_angle_gamma                94.7301(11)
_cell_volume                     508.363(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    14839
_cell_measurement_theta_min      3.824
_cell_measurement_theta_max      77.269

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.048
_exptl_crystal_density_diffrn    2.123
_exptl_crystal_F_000             306
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -4 7 0.0254
0 7 -3 0.0206
-3 1 -1 0.0667
0 4 -8 0.0449
-3 0 0 0.0713
3 0 0 0.0225
0 -6 -2 0.0356
0 -4 -5 0.0281
0 -6 -1 0.0337
0 6 2 0.0131


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    29.178
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
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_correction_T_min  0.134
_exptl_absorpt_correction_T_max  0.445
_shelx_estimated_absorpt_T_min   0.128
_shelx_estimated_absorpt_T_max   0.335

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      250(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0161373
_diffrn_orient_matrix_ub_12      -0.0138761
_diffrn_orient_matrix_ub_13      -0.1287911
_diffrn_orient_matrix_ub_21      0.0280246
_diffrn_orient_matrix_ub_22      0.151045
_diffrn_orient_matrix_ub_23      0.0362397
_diffrn_orient_matrix_ub_31      0.3804931
_diffrn_orient_matrix_ub_32      0.0043114
_diffrn_orient_matrix_ub_33      0.0025479
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_number            18807
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.839
_diffrn_reflns_theta_max         77.278
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.96
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.96
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.96
_reflns_Friedel_coverage         0
_reflns_number_total             2068
_reflns_number_gt                2001
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0433P)²+0.2215P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0028(3)
_refine_ls_number_reflns         2068
_refine_ls_number_parameters     173
_refine_ls_number_restraints     351
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0657
_refine_ls_wR_factor_gt          0.0639
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_restrained_S_all      0.964
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         0.693
_refine_diff_density_min         -1.001
_refine_diff_density_rms         0.099

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 The 4,4'-vinylenedipyridine molecule is undergoing detectable pedal motion at
 this temperature. The major and minor positions of the disorder (A and B sites) 
 were allowed to refine their occupancies to a total value of 1. The A and B
 sites had occupancies of 0.93 and 0.07, respectively. To help model this 
 disorder and maintain reasonable ADP values SIMU, RIGU, DFIX and AFIX 
 restraints and constraints were applied. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.71145(5) 0.71074(2) 0.28751(2) 0.03754(12) Uani 1 1 d . . . . .
Cl1 Cl 0.4095(3) 0.73437(8) 0.54173(8) 0.0479(2) Uani 1 1 d . . . . .
Cl2 Cl 0.2319(2) 0.98744(8) 0.72817(7) 0.0448(2) Uani 1 1 d . . . . .
C1 C 0.5858(8) 0.8834(3) 0.4144(3) 0.0319(6) Uani 1 1 d . . . . .
C2 C 0.4624(8) 0.8813(3) 0.5171(3) 0.0320(6) Uani 1 1 d . . . . .
C3 C 0.3797(8) 0.9951(3) 0.6015(3) 0.0313(6) Uani 1 1 d . . . . .
N1A N 0.8846(12) 0.4541(3) 0.1431(4) 0.0431(9) Uani 0.935(8) 1 d . U P A 1
C4A C 1.0441(14) 0.4076(4) 0.2156(4) 0.0455(10) Uani 0.935(8) 1 d . U P A 1
H4A H 1.113552 0.466388 0.291089 0.055 Uiso 0.935(8) 1 calc R U P A 1
C5A C 1.1117(11) 0.2789(4) 0.1857(4) 0.0425(9) Uani 0.935(8) 1 d . U P A 1
H5A H 1.225556 0.251656 0.239878 0.051 Uiso 0.935(8) 1 calc R U P A 1
C6A C 1.0102(11) 0.1889(3) 0.0745(4) 0.0335(8) Uani 0.935(8) 1 d D U P A 1
C7A C 0.8458(12) 0.2367(4) -0.0006(3) 0.0379(8) Uani 0.935(8) 1 d . U P A 1
H7A H 0.771886 0.180231 -0.076425 0.046 Uiso 0.935(8) 1 calc R U P A 1
C8A C 0.7913(12) 0.3685(4) 0.0371(4) 0.0427(9) Uani 0.935(8) 1 d . U P A 1
H8A H 0.681775 0.399106 -0.015647 0.051 Uiso 0.935(8) 1 calc R U P A 1
C9A C 1.0770(9) 0.0507(3) 0.0437(3) 0.0349(9) Uani 0.935(8) 1 d D U P A 1
H9A H 1.243088 0.03268 0.08981 0.042 Uiso 0.935(8) 1 calc R U P A 1
N1B N 0.950(19) 0.459(3) 0.155(6) 0.043(3) Uani 0.065(8) 1 d G U P A 2
C4B C 1.094(17) 0.380(6) 0.207(4) 0.043(3) Uani 0.065(8) 1 d G U P A 2
H4B H 1.202497 0.417994 0.281433 0.051 Uiso 0.065(8) 1 calc R U P A 2
C5B C 1.077(14) 0.245(5) 0.148(5) 0.038(3) Uani 0.065(8) 1 d G U P A 2
H5B H 1.174625 0.191319 0.182756 0.045 Uiso 0.065(8) 1 calc R U P A 2
C6B C 0.916(14) 0.188(3) 0.037(5) 0.035(3) Uani 0.065(8) 1 d DG U P A 2
C7B C 0.772(13) 0.267(5) -0.015(4) 0.037(3) Uani 0.065(8) 1 d G U P A 2
H7B H 0.663438 0.22925 -0.089727 0.045 Uiso 0.065(8) 1 calc R U P A 2
C8B C 0.789(16) 0.403(4) 0.044(6) 0.041(3) Uani 0.065(8) 1 d G U P A 2
H8B H 0.691308 0.455927 0.008948 0.049 Uiso 0.065(8) 1 calc R U P A 2
C9B C 0.932(11) 0.045(3) -0.014(4) 0.033(4) Uani 0.065(8) 1 d D U P A 2
H9B H 0.80883 0.008637 -0.086259 0.04 Uiso 0.065(8) 1 calc R U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 2.100(3) . ?
I1 N1A 2.903(4) . ?
I1 N1B 2.93(4) . ?
Cl1 C2 1.732(3) . ?
Cl2 C3 1.726(3) . ?
C1 C2 1.392(4) . ?
C1 C3 1.404(4) 2_676 ?
C2 C3 1.389(4) . ?
N1A C8A 1.328(5) . ?
N1A C4A 1.341(6) . ?
C4A C5A 1.375(5) . ?
C4A H4A 0.94 . ?
C5A C6A 1.396(5) . ?
C5A H5A 0.94 . ?
C6A C7A 1.385(5) . ?
C6A C9A 1.471(4) . ?
C7A C8A 1.387(5) . ?
C7A H7A 0.94 . ?
C8A H8A 0.94 . ?
C9A C9A 1.328(7) 2_755 ?
C9A H9A 0.94 . ?
N1B C4B 1.39 . ?
N1B C8B 1.39 . ?
C4B C5B 1.39 . ?
C4B H4B 0.94 . ?
C5B C6B 1.39 . ?
C5B H5B 0.94 . ?
C6B C7B 1.39 . ?
C6B C9B 1.47(3) . ?
C7B C8B 1.39 . ?
C7B H7B 0.94 . ?
C8B H8B 0.94 . ?
C9B C9B 1.31(3) 2_755 ?
C9B H9B 0.94 . ?

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
C1 I1 N1A 170.37(14) . . ?
C1 I1 N1B 167.4(14) . . ?
C2 C1 C3 117.5(3) . 2_676 ?
C2 C1 I1 121.1(2) . . ?
C3 C1 I1 121.4(2) 2_676 . ?
C3 C2 C1 121.4(3) . . ?
C3 C2 Cl1 118.7(2) . . ?
C1 C2 Cl1 119.9(2) . . ?
C2 C3 C1 121.1(3) . 2_676 ?
C2 C3 Cl2 119.5(2) . . ?
C1 C3 Cl2 119.3(2) 2_676 . ?
C8A N1A C4A 116.5(3) . . ?
C8A N1A I1 136.1(3) . . ?
C4A N1A I1 105.6(3) . . ?
N1A C4A C5A 123.7(4) . . ?
N1A C4A H4A 118.2 . . ?
C5A C4A H4A 118.2 . . ?
C4A C5A C6A 119.6(4) . . ?
C4A C5A H5A 120.2 . . ?
C6A C5A H5A 120.2 . . ?
C7A C6A C5A 116.8(3) . . ?
C7A C6A C9A 123.8(4) . . ?
C5A C6A C9A 119.4(4) . . ?
C6A C7A C8A 119.5(3) . . ?
C6A C7A H7A 120.3 . . ?
C8A C7A H7A 120.3 . . ?
N1A C8A C7A 123.9(4) . . ?
N1A C8A H8A 118.1 . . ?
C7A C8A H8A 118.1 . . ?
C9A C9A C6A 125.6(4) 2_755 . ?
C9A C9A H9A 117.2 2_755 . ?
C6A C9A H9A 117.2 . . ?
C4B N1B C8B 120 . . ?
C4B N1B I1 123(3) . . ?
C8B N1B I1 112(3) . . ?
C5B C4B N1B 120 . . ?
C5B C4B H4B 120 . . ?
N1B C4B H4B 120 . . ?
C4B C5B C6B 120 . . ?
C4B C5B H5B 120 . . ?
C6B C5B H5B 120 . . ?
C5B C6B C7B 120 . . ?
C5B C6B C9B 113(4) . . ?
C7B C6B C9B 127(4) . . ?
C8B C7B C6B 120 . . ?
C8B C7B H7B 120 . . ?
C6B C7B H7B 120 . . ?
C7B C8B N1B 120 . . ?
C7B C8B H8B 120 . . ?
N1B C8B H8B 120 . . ?
C9B C9B C6B 138(6) 2_755 . ?
C9B C9B H9B 111.1 2_755 . ?
C6B C9B H9B 111.1 . . ?

####################################################################### 
# 
# 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_hut19_49_270
_database_code_depnum_ccdc_archive 'CCDC 1954982'
loop_
_audit_author_name
_audit_author_address
'Daniel K. Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-09-20 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;

_audit_creation_date             2019-09-06T14:46:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C9 H5 Cl2 I N'
_chemical_formula_weight         324.94

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.07136(7)
_cell_length_b                   10.92294(16)
_cell_length_c                   12.36101(14)
_cell_angle_alpha                110.7818(12)
_cell_angle_beta                 92.5300(13)
_cell_angle_gamma                94.8692(13)
_cell_volume                     510.460(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    14645
_cell_measurement_theta_min      3.812
_cell_measurement_theta_max      77.217

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.048
_exptl_crystal_density_diffrn    2.114
_exptl_crystal_F_000             306
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -4 7 0.0254
0 7 -3 0.0206
-3 1 -1 0.0667
0 4 -8 0.0449
-3 0 0 0.0713
3 0 0 0.0225
0 -6 -2 0.0356
0 -4 -5 0.0281
0 -6 -1 0.0337
0 6 2 0.0131


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    29.058
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
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_correction_T_min  0.134
_exptl_absorpt_correction_T_max  0.446
_shelx_estimated_absorpt_T_min   0.128
_shelx_estimated_absorpt_T_max   0.336

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      270(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0162561
_diffrn_orient_matrix_ub_12      -0.0138911
_diffrn_orient_matrix_ub_13      -0.1286308
_diffrn_orient_matrix_ub_21      0.0293302
_diffrn_orient_matrix_ub_22      0.151042
_diffrn_orient_matrix_ub_23      0.0364965
_diffrn_orient_matrix_ub_31      0.379494
_diffrn_orient_matrix_ub_32      0.0041286
_diffrn_orient_matrix_ub_33      0.002371
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_number            19057
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.837
_diffrn_reflns_theta_max         77.373
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.958
_reflns_Friedel_coverage         0
_reflns_number_total             2081
_reflns_number_gt                1979
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0433P)²+0.2215P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0030(3)
_refine_ls_number_reflns         2081
_refine_ls_number_parameters     172
_refine_ls_number_restraints     343
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0253
_refine_ls_wR_factor_ref         0.0672
_refine_ls_wR_factor_gt          0.0646
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_restrained_S_all      0.967
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.9
_refine_diff_density_rms         0.099

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 The 4,4'-vinylenedipyridine molecule is undergoing detectable pedal motion at
 this temperature. The major and minor positions of the disorder (A and B sites) 
 were allowed to refine their occupancies to a total value of 1. The A and B
 sites had occupancies of 0.90 and 0.10, respectively. To help model this 
 disorder and maintain reasonable ADP values SIMU, RIGU, DFIX and AFIX 
 restraints and constraints were applied. During the final refinements, the 
 inconsistent reflection 4 -5 8 was omitted. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.71291(5) 0.71080(2) 0.28815(2) 0.04136(12) Uani 1 1 d . . . . .
Cl1 Cl 0.4129(3) 0.73509(8) 0.54233(8) 0.0526(2) Uani 1 1 d . . . . .
Cl2 Cl 0.2332(2) 0.98803(9) 0.72818(7) 0.0492(2) Uani 1 1 d . . . . .
C1 C 0.5864(8) 0.8835(3) 0.4145(3) 0.0349(6) Uani 1 1 d . . . . .
C2 C 0.4633(8) 0.8816(3) 0.5171(3) 0.0353(6) Uani 1 1 d . . . . .
C3 C 0.3800(8) 0.9955(3) 0.6014(3) 0.0342(6) Uani 1 1 d . . . . .
N1A N 0.8827(12) 0.4537(4) 0.1440(5) 0.0466(11) Uani 0.899(10) 1 d . U P A 1
C4A C 1.0394(14) 0.4071(5) 0.2162(4) 0.0496(11) Uani 0.899(10) 1 d . U P A 1
H4A H 1.10481 0.465003 0.291228 0.059 Uiso 0.899(10) 1 calc R U P A 1
C5A C 1.1095(13) 0.2791(5) 0.1862(4) 0.0469(10) Uani 0.899(10) 1 d . U P A 1
H5A H 1.222644 0.252633 0.239683 0.056 Uiso 0.899(10) 1 calc R U P A 1
C6A C 1.0104(12) 0.1891(4) 0.0753(4) 0.0375(9) Uani 0.899(10) 1 d D U P A 1
C7A C 0.8458(13) 0.2363(4) 0.0001(4) 0.0421(10) Uani 0.899(10) 1 d . U P A 1
H7A H 0.772915 0.180494 -0.074976 0.05 Uiso 0.899(10) 1 calc R U P A 1
C8A C 0.7913(15) 0.3681(5) 0.0386(5) 0.0470(10) Uani 0.899(10) 1 d . U P A 1
H8A H 0.683002 0.39827 -0.01336 0.056 Uiso 0.899(10) 1 calc R U P A 1
C9A C 1.0758(11) 0.0506(3) 0.0438(4) 0.0376(10) Uani 0.899(10) 1 d D U P A 1
H9A H 1.238317 0.032625 0.089645 0.045 Uiso 0.899(10) 1 calc R U P A 1
N1B N 0.958(12) 0.459(2) 0.140(4) 0.047(3) Uani 0.101(10) 1 d G U P A 2
C4B C 1.106(11) 0.390(4) 0.200(3) 0.046(3) Uani 0.101(10) 1 d G U P A 2
H4B H 1.214482 0.43397 0.273366 0.055 Uiso 0.101(10) 1 calc R U P A 2
C5B C 1.091(10) 0.253(4) 0.151(3) 0.042(3) Uani 0.101(10) 1 d G U P A 2
H5B H 1.190485 0.206344 0.190795 0.051 Uiso 0.101(10) 1 calc R U P A 2
C6B C 0.929(10) 0.187(2) 0.042(3) 0.039(3) Uani 0.101(10) 1 d DG U P A 2
C7B C 0.781(10) 0.257(4) -0.018(3) 0.041(3) Uani 0.101(10) 1 d G U P A 2
H7B H 0.672399 0.21213 -0.091362 0.049 Uiso 0.101(10) 1 calc R U P A 2
C8B C 0.795(12) 0.393(4) 0.031(4) 0.045(3) Uani 0.101(10) 1 d G U P A 2
H8B H 0.696394 0.439757 -0.008793 0.054 Uiso 0.101(10) 1 calc R U P A 2
C9B C 0.932(10) 0.043(3) -0.011(3) 0.038(3) Uani 0.101(10) 1 d D U P A 2
H9B H 0.792416 0.007219 -0.078611 0.046 Uiso 0.101(10) 1 calc R U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 2.100(3) . ?
I1 N1A 2.903(4) . ?
I1 N1B 2.99(3) . ?
Cl1 C2 1.733(3) . ?
Cl2 C3 1.728(3) . ?
C1 C2 1.390(4) . ?
C1 C3 1.401(4) 2_676 ?
C2 C3 1.389(4) . ?
N1A C8A 1.321(6) . ?
N1A C4A 1.337(6) . ?
C4A C5A 1.373(6) . ?
C4A H4A 0.93 . ?
C5A C6A 1.391(6) . ?
C5A H5A 0.93 . ?
C6A C7A 1.387(6) . ?
C6A C9A 1.473(5) . ?
C7A C8A 1.388(5) . ?
C7A H7A 0.93 . ?
C8A H8A 0.93 . ?
C9A C9A 1.323(9) 2_755 ?
C9A H9A 0.93 . ?
N1B C4B 1.39 . ?
N1B C8B 1.39 . ?
C4B C5B 1.39 . ?
C4B H4B 0.93 . ?
C5B C6B 1.39 . ?
C5B H5B 0.93 . ?
C6B C7B 1.39 . ?
C6B C9B 1.47(2) . ?
C7B C8B 1.39 . ?
C7B H7B 0.93 . ?
C8B H8B 0.93 . ?
C9B C9B 1.23(7) 2_755 ?
C9B H9B 0.93 . ?

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
C1 I1 N1A 170.36(14) . . ?
C1 I1 N1B 170.5(9) . . ?
C2 C1 C3 117.4(3) . 2_676 ?
C2 C1 I1 121.1(2) . . ?
C3 C1 I1 121.5(2) 2_676 . ?
C3 C2 C1 121.4(3) . . ?
C3 C2 Cl1 118.6(2) . . ?
C1 C2 Cl1 119.9(2) . . ?
C2 C3 C1 121.1(3) . 2_676 ?
C2 C3 Cl2 119.5(2) . . ?
C1 C3 Cl2 119.3(2) 2_676 . ?
C8A N1A C4A 116.1(4) . . ?
C8A N1A I1 136.4(4) . . ?
C4A N1A I1 105.8(3) . . ?
N1A C4A C5A 124.0(4) . . ?
N1A C4A H4A 118 . . ?
C5A C4A H4A 118 . . ?
C4A C5A C6A 119.7(4) . . ?
C4A C5A H5A 120.2 . . ?
C6A C5A H5A 120.2 . . ?
C7A C6A C5A 116.7(3) . . ?
C7A C6A C9A 123.4(4) . . ?
C5A C6A C9A 119.9(4) . . ?
C6A C7A C8A 119.0(4) . . ?
C6A C7A H7A 120.5 . . ?
C8A C7A H7A 120.5 . . ?
N1A C8A C7A 124.4(4) . . ?
N1A C8A H8A 117.8 . . ?
C7A C8A H8A 117.8 . . ?
C9A C9A C6A 125.9(5) 2_755 . ?
C9A C9A H9A 117.1 2_755 . ?
C6A C9A H9A 117.1 . . ?
C4B N1B C8B 120 . . ?
C4B N1B I1 116(2) . . ?
C8B N1B I1 118(2) . . ?
C5B C4B N1B 120 . . ?
C5B C4B H4B 120 . . ?
N1B C4B H4B 120 . . ?
C6B C5B C4B 120 . . ?
C6B C5B H5B 120 . . ?
C4B C5B H5B 120 . . ?
C5B C6B C7B 120 . . ?
C5B C6B C9B 119(3) . . ?
C7B C6B C9B 121(3) . . ?
C8B C7B C6B 120 . . ?
C8B C7B H7B 120 . . ?
C6B C7B H7B 120 . . ?
C7B C8B N1B 120 . . ?
C7B C8B H8B 120 . . ?
N1B C8B H8B 120 . . ?
C9B C9B C6B 137(5) 2_755 . ?
C9B C9B H9B 111.4 2_755 . ?
C6B C9B H9B 111.4 . . ?

####################################################################### 
# 
# 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_hut19_49_230
_database_code_depnum_ccdc_archive 'CCDC 1954980'
loop_
_audit_author_name
_audit_author_address
'Daniel K. Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-09-20 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;

_audit_creation_date             2019-09-06T14:45:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H10 Cl4 I2 N2'
_chemical_formula_weight         649.88

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.05144(5)
_cell_length_b                   10.90047(11)
_cell_length_c                   12.32575(11)
_cell_angle_alpha                110.5582(9)
_cell_angle_beta                 92.6207(9)
_cell_angle_gamma                94.6300(9)
_cell_volume                     506.406(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    15186
_cell_measurement_theta_min      3.819
_cell_measurement_theta_max      77.164

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.048
_exptl_crystal_density_diffrn    2.131
_exptl_crystal_F_000             306
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -4 7 0.0254
0 7 -3 0.0206
-3 1 -1 0.0667
0 4 -8 0.0449
-3 0 0 0.0713
3 0 0 0.0225
0 -6 -2 0.0356
0 -4 -5 0.0281
0 -6 -1 0.0337
0 6 2 0.0131


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    29.291
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
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_correction_T_min  0.134
_exptl_absorpt_correction_T_max  0.445
_shelx_estimated_absorpt_T_min   0.127
_shelx_estimated_absorpt_T_max   0.334

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      230(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.016034
_diffrn_orient_matrix_ub_12      -0.013696
_diffrn_orient_matrix_ub_13      -0.1289043
_diffrn_orient_matrix_ub_21      0.0269996
_diffrn_orient_matrix_ub_22      0.1510711
_diffrn_orient_matrix_ub_23      0.0361743
_diffrn_orient_matrix_ub_31      0.3814117
_diffrn_orient_matrix_ub_32      0.0044851
_diffrn_orient_matrix_ub_33      0.0026844
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_number            18963
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.842
_diffrn_reflns_theta_max         77.16
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_reflns_Friedel_coverage         0
_reflns_number_total             2064
_reflns_number_gt                1995
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0433P)²+0.2215P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0030(3)
_refine_ls_number_reflns         2064
_refine_ls_number_parameters     173
_refine_ls_number_restraints     351
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0248
_refine_ls_wR_factor_ref         0.0663
_refine_ls_wR_factor_gt          0.0638
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.955
_refine_diff_density_rms         0.107

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 The 4,4'-vinylenedipyridine molecule is undergoing detectable pedal motion at
 this temperature. The major and minor positions of the disorder (A and B sites) 
 were allowed to refine their occupancies to a total value of 1. The A and B
 sites had occupancies of 0.96 and 0.04, respectively. To help model this 
 disorder and maintain reasonable ADP values SIMU, RIGU, DFIX and AFIX 
 restraints and constraints were applied. 
;


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.71020(5) 0.71065(2) 0.28702(2) 0.03388(12) Uani 1 1 d . . . . .
Cl1 Cl 0.4065(3) 0.73390(8) 0.54135(7) 0.0431(2) Uani 1 1 d . . . . .
Cl2 Cl 0.2306(2) 0.98696(8) 0.72829(7) 0.0407(2) Uani 1 1 d . . . . .
C1 C 0.5846(8) 0.8833(3) 0.4138(3) 0.0293(6) Uani 1 1 d . . . . .
C2 C 0.4608(8) 0.8812(3) 0.5171(3) 0.0295(6) Uani 1 1 d . . . . .
C3 C 0.3790(8) 0.9948(3) 0.6015(3) 0.0290(6) Uani 1 1 d . . . . .
N1A N 0.8849(10) 0.4545(3) 0.1436(3) 0.0394(9) Uani 0.963(8) 1 d . U P A 1
C4A C 1.0436(12) 0.4071(4) 0.2156(4) 0.0414(10) Uani 0.963(8) 1 d . U P A 1
H4A H 1.111114 0.46533 0.291428 0.05 Uiso 0.963(8) 1 calc R U P A 1
C5A C 1.1139(11) 0.2787(4) 0.1858(4) 0.0387(9) Uani 0.963(8) 1 d . U P A 1
H5A H 1.230221 0.251552 0.239708 0.046 Uiso 0.963(8) 1 calc R U P A 1
C6A C 1.0110(10) 0.1891(3) 0.0746(4) 0.0310(8) Uani 0.963(8) 1 d D U P A 1
C7A C 0.8449(11) 0.2374(4) -0.0003(3) 0.0353(8) Uani 0.963(8) 1 d . U P A 1
H7A H 0.770059 0.181214 -0.076218 0.042 Uiso 0.963(8) 1 calc R U P A 1
C8A C 0.7901(11) 0.3694(4) 0.0376(4) 0.0395(8) Uani 0.963(8) 1 d . U P A 1
H8A H 0.679492 0.400306 -0.01491 0.047 Uiso 0.963(8) 1 calc R U P A 1
C9A C 1.0781(9) 0.0507(3) 0.0438(3) 0.0317(8) Uani 0.963(8) 1 d D U P A 1
H9A H 1.244989 0.032416 0.089749 0.038 Uiso 0.963(8) 1 calc R U P A 1
N1B N 0.97(3) 0.464(5) 0.137(8) 0.039(3) Uani 0.037(8) 1 d G U P A 2
C4B C 1.11(3) 0.391(8) 0.197(7) 0.039(3) Uani 0.037(8) 1 d G U P A 2
H4B H 1.218027 0.434387 0.271652 0.047 Uiso 0.037(8) 1 calc R U P A 2
C5B C 1.08(2) 0.255(8) 0.148(8) 0.036(3) Uani 0.037(8) 1 d G U P A 2
H5B H 1.172747 0.205348 0.188549 0.043 Uiso 0.037(8) 1 calc R U P A 2
C6B C 0.92(2) 0.191(5) 0.038(8) 0.033(3) Uani 0.037(8) 1 d DG U P A 2
C7B C 0.78(2) 0.264(7) -0.022(6) 0.035(3) Uani 0.037(8) 1 d G U P A 2
H7B H 0.673233 0.220807 -0.096474 0.042 Uiso 0.037(8) 1 calc R U P A 2
C8B C 0.81(2) 0.401(7) 0.027(8) 0.038(3) Uani 0.037(8) 1 d G U P A 2
H8B H 0.71851 0.449847 -0.013372 0.045 Uiso 0.037(8) 1 calc R U P A 2
C9B C 0.94(2) 0.049(5) -0.013(6) 0.031(4) Uani 0.037(8) 1 d D U P A 2
H9B H 0.84993 0.016019 -0.090491 0.037 Uiso 0.037(8) 1 calc R U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 2.099(3) . ?
I1 N1A 2.896(3) . ?
I1 N1B 2.99(7) . ?
Cl1 C2 1.733(3) . ?
Cl2 C3 1.727(3) . ?
C1 C2 1.396(4) . ?
C1 C3 1.404(4) 2_676 ?
C2 C3 1.385(4) . ?
N1A C8A 1.327(5) . ?
N1A C4A 1.339(5) . ?
C4A C5A 1.373(5) . ?
C4A H4A 0.94 . ?
C5A C6A 1.396(5) . ?
C5A H5A 0.94 . ?
C6A C7A 1.388(5) . ?
C6A C9A 1.472(4) . ?
C7A C8A 1.388(5) . ?
C7A H7A 0.94 . ?
C8A H8A 0.94 . ?
C9A C9A 1.333(7) 2_755 ?
C9A H9A 0.94 . ?
N1B C4B 1.39 . ?
N1B C8B 1.39 . ?
C4B C5B 1.39 . ?
C4B H4B 0.94 . ?
C5B C6B 1.39 . ?
C5B H5B 0.94 . ?
C6B C7B 1.39 . ?
C6B C9B 1.47(3) . ?
C7B C8B 1.39 . ?
C7B H7B 0.94 . ?
C8B H8B 0.94 . ?
C9B C9B 1.32(3) 2_755 ?
C9B H9B 0.94 . ?

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
C1 I1 N1A 170.23(12) . . ?
C1 I1 N1B 170.4(19) . . ?
C2 C1 C3 117.3(3) . 2_676 ?
C2 C1 I1 121.1(2) . . ?
C3 C1 I1 121.6(2) 2_676 . ?
C3 C2 C1 121.5(3) . . ?
C3 C2 Cl1 118.7(2) . . ?
C1 C2 Cl1 119.8(2) . . ?
C2 C3 C1 121.2(3) . 2_676 ?
C2 C3 Cl2 119.6(2) . . ?
C1 C3 Cl2 119.2(2) 2_676 . ?
C8A N1A C4A 116.4(3) . . ?
C8A N1A I1 135.7(3) . . ?
C4A N1A I1 106.1(2) . . ?
N1A C4A C5A 124.2(3) . . ?
N1A C4A H4A 117.9 . . ?
C5A C4A H4A 117.9 . . ?
C4A C5A C6A 119.3(3) . . ?
C4A C5A H5A 120.3 . . ?
C6A C5A H5A 120.3 . . ?
C7A C6A C5A 116.8(3) . . ?
C7A C6A C9A 123.9(4) . . ?
C5A C6A C9A 119.3(4) . . ?
C8A C7A C6A 119.5(3) . . ?
C8A C7A H7A 120.3 . . ?
C6A C7A H7A 120.3 . . ?
N1A C8A C7A 123.8(3) . . ?
N1A C8A H8A 118.1 . . ?
C7A C8A H8A 118.1 . . ?
C9A C9A C6A 125.4(4) 2_755 . ?
C9A C9A H9A 117.3 2_755 . ?
C6A C9A H9A 117.3 . . ?
C4B N1B C8B 120 . . ?
C4B N1B I1 115(5) . . ?
C8B N1B I1 117(5) . . ?
C5B C4B N1B 120 . . ?
C5B C4B H4B 120 . . ?
N1B C4B H4B 120 . . ?
C6B C5B C4B 120 . . ?
C6B C5B H5B 120 . . ?
C4B C5B H5B 120 . . ?
C5B C6B C7B 120 . . ?
C5B C6B C9B 116(7) . . ?
C7B C6B C9B 124(7) . . ?
C6B C7B C8B 120 . . ?
C6B C7B H7B 120 . . ?
C8B C7B H7B 120 . . ?
C7B C8B N1B 120 . . ?
C7B C8B H8B 120 . . ?
N1B C8B H8B 120 . . ?
C9B C9B C6B 141(9) 2_755 . ?
C9B C9B H9B 109.6 2_755 . ?
C6B C9B H9B 109.6 . . ?

####################################################################### 
# 
# 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_eb889190_a
_database_code_depnum_ccdc_archive 'CCDC 1955223'
loop_
_audit_author_name
_audit_author_address
'Daniel K. Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            
'Cocrystal 1,2,4,5-tetrachlorobenzene and 1,2-bis(4-pyridyl)ethyne'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 N2, C6 Cl4 I2'
_chemical_formula_sum            'C18 H8 Cl4 I2 N2'
_chemical_formula_weight         647.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   4.0179(2)
_cell_length_b                   11.1807(6)
_cell_length_c                   12.1538(7)
_cell_angle_alpha                111.5050(10)
_cell_angle_beta                 90.5190(10)
_cell_angle_gamma                97.6160(10)
_cell_volume                     502.51(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    5176
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      27.31

_exptl_crystal_description       cut
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.141
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.03
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_max          0.30
_exptl_absorpt_coefficient_mu    3.666
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.706
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS V2014(Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3660

_diffrn_reflns_number            6295
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.804
_diffrn_reflns_theta_max         27.313
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2261
_reflns_number_gt                2195
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'XSeed (Barbour, 2001)'
_computing_publication_material  'XSeed (Barbour, 2001)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0156P)²+0.1270P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2261
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0133
_refine_ls_R_factor_gt           0.0126
_refine_ls_wR_factor_ref         0.0318
_refine_ls_wR_factor_gt          0.0315
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.21502(2) 0.70915(2) 0.79362(2) 0.02025(4) Uani 1 1 d . . . . .
Cl1 Cl 0.28455(11) 0.99786(4) 0.76177(3) 0.02688(9) Uani 1 1 d . . . . .
N1 N 0.3741(4) 0.45466(14) 0.64801(14) 0.0279(3) Uani 1 1 d . . . . .
C1 C 0.3075(4) 0.24624(16) 0.48973(15) 0.0245(3) Uani 1 1 d . . . . .
H1 H 0.234583 0.194671 0.409738 0.029 Uiso 1 1 calc R U . . .
Cl2 Cl 0.09440(12) 1.25114(4) 0.94156(4) 0.02788(9) Uani 1 1 d . . . . .
C2 C 0.2764(4) 0.37709(17) 0.53659(16) 0.0264(4) Uani 1 1 d . . . . .
H2 H 0.180355 0.413557 0.486656 0.032 Uiso 1 1 calc R U . . .
C3 C 0.5114(5) 0.40218(17) 0.71700(16) 0.0287(4) Uani 1 1 d . . . . .
H3 H 0.584203 0.456752 0.796257 0.034 Uiso 1 1 calc R U . . .
C4 C 0.5529(5) 0.27255(16) 0.67901(15) 0.0260(4) Uani 1 1 d . . . . .
H4 H 0.650782 0.239294 0.731210 0.031 Uiso 1 1 calc R U . . .
C5 C 0.4483(4) 0.19163(15) 0.56252(14) 0.0207(3) Uani 1 1 d . . . . .
C6 C 0.4851(4) 0.05617(16) 0.51819(15) 0.0237(3) Uani 1 1 d . . . . .
C7 C 0.0890(4) 0.88346(15) 0.91708(13) 0.0179(3) Uani 1 1 d . . . . .
C8 C 0.1276(4) 0.99780(15) 0.89348(13) 0.0180(3) Uani 1 1 d . . . . .
C9 C 0.0400(4) 1.11275(15) 0.97545(13) 0.0184(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C7 2.1065(15) . ?
Cl1 C8 1.7259(16) . ?
N1 C2 1.334(2) . ?
N1 C3 1.338(2) . ?
C1 C2 1.385(2) . ?
C1 C5 1.398(2) . ?
Cl2 C9 1.7294(16) . ?
C3 C4 1.384(2) . ?
C4 C5 1.396(2) . ?
C5 C6 1.438(2) . ?
C6 C6 1.192(3) 2_656 ?
C7 C9 1.398(2) 2_577 ?
C7 C8 1.399(2) . ?
C8 C9 1.399(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C3 117.54(15) . . ?
C2 C1 C5 118.66(16) . . ?
N1 C2 C1 123.57(16) . . ?
N1 C3 C4 123.48(17) . . ?
C3 C4 C5 118.74(16) . . ?
C4 C5 C1 118.02(15) . . ?
C4 C5 C6 121.18(15) . . ?
C1 C5 C6 120.80(15) . . ?
C6 C6 C5 179.7(3) 2_656 . ?
C9 C7 C8 118.22(14) 2_577 . ?
C9 C7 I1 120.58(11) 2_577 . ?
C8 C7 I1 121.20(11) . . ?
C9 C8 C7 120.80(14) . . ?
C9 C8 Cl1 119.26(12) . . ?
C7 C8 Cl1 119.94(12) . . ?
C7 C9 C8 120.98(14) 2_577 . ?
C7 C9 Cl2 120.30(12) 2_577 . ?
C8 C9 Cl2 118.72(12) . . ?

_refine_diff_density_max         0.461
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_eb886250_a
_database_code_depnum_ccdc_archive 'CCDC 1955226'
loop_
_audit_author_name
_audit_author_address
'Daniel K. Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            
'Cocrystal 1,2,4,5-tetrachlorobenzene and 1,2-bis(4-pyridyl)ethyne'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 N2, C6 Cl4 I2'
_chemical_formula_sum            'C18 H8 Cl4 I2 N2'
_chemical_formula_weight         647.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   4.0413(2)
_cell_length_b                   11.1833(6)
_cell_length_c                   12.1828(7)
_cell_angle_alpha                111.4890(10)
_cell_angle_beta                 90.6370(10)
_cell_angle_gamma                97.4090(10)
_cell_volume                     507.03(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    4869
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      27.24

_exptl_crystal_description       cut
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.122
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.03
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_max          0.30
_exptl_absorpt_coefficient_mu    3.634
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.705
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS V2014(Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3660

_diffrn_reflns_number            6351
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.800
_diffrn_reflns_theta_max         27.223
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2267
_reflns_number_gt                2191
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'XSeed (Barbour, 2001)'
_computing_publication_material  'XSeed (Barbour, 2001)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0165P)²+0.1762P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2267
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0154
_refine_ls_R_factor_gt           0.0146
_refine_ls_wR_factor_ref         0.0349
_refine_ls_wR_factor_gt          0.0345
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.28512(3) 0.29044(2) 0.70587(2) 0.02779(5) Uani 1 1 d . . . . .
Cl1 Cl 0.59136(14) 0.25082(5) 0.44190(4) 0.03771(11) Uani 1 1 d . . . . .
N1 N 0.1257(5) 0.54579(15) 0.85220(16) 0.0372(4) Uani 1 1 d . . . . .
Cl2 Cl 0.78111(13) -0.00217(5) 0.26245(4) 0.03631(11) Uani 1 1 d . . . . .
C2 C 0.1924(5) 0.75392(19) 1.00956(17) 0.0328(4) Uani 1 1 d . . . . .
H2 H 0.265439 0.804882 1.088392 0.039 Uiso 1 1 calc R U . . .
C3 C 0.2230(5) 0.62328(19) 0.96282(19) 0.0354(4) Uani 1 1 d . . . . .
H3 H 0.318094 0.587214 1.012129 0.042 Uiso 1 1 calc R U . . .
C4 C -0.0106(6) 0.59861(19) 0.78384(18) 0.0382(5) Uani 1 1 d . . . . .
H4 H -0.081342 0.544845 0.705485 0.046 Uiso 1 1 calc R U . . .
C5 C -0.0538(5) 0.72799(19) 0.82165(18) 0.0352(4) Uani 1 1 d . . . . .
H5 H -0.151839 0.760869 0.770322 0.042 Uiso 1 1 calc R U . . .
C6 C 0.0513(5) 0.80839(17) 0.93756(16) 0.0276(4) Uani 1 1 d . . . . .
C7 C 0.0149(5) 0.94393(18) 0.98188(17) 0.0314(4) Uani 1 1 d . . . . .
C8 C 0.4117(4) 0.11662(16) 0.58265(15) 0.0231(3) Uani 1 1 d . . . . .
C9 C 0.5387(4) 0.11269(17) 0.47571(15) 0.0241(3) Uani 1 1 d . . . . .
C10 C 0.6259(4) -0.00245(17) 0.39395(15) 0.0242(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C8 2.1046(16) . ?
Cl1 C9 1.7275(18) . ?
N1 C3 1.329(3) . ?
N1 C4 1.334(3) . ?
Cl2 C10 1.7277(18) . ?
C2 C3 1.383(3) . ?
C2 C6 1.391(3) . ?
C4 C5 1.384(3) . ?
C5 C6 1.393(3) . ?
C6 C7 1.439(2) . ?
C7 C7 1.190(4) 2_577 ?
C8 C9 1.393(2) . ?
C8 C10 1.397(2) 2_656 ?
C9 C10 1.400(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C4 117.21(17) . . ?
C3 C2 C6 118.66(18) . . ?
N1 C3 C2 123.78(18) . . ?
N1 C4 C5 123.77(19) . . ?
C4 C5 C6 118.45(18) . . ?
C2 C6 C5 118.12(17) . . ?
C2 C6 C7 120.81(17) . . ?
C5 C6 C7 121.07(17) . . ?
C7 C7 C6 179.7(3) 2_577 . ?
C9 C8 C10 118.15(15) . 2_656 ?
C9 C8 I1 120.75(13) . . ?
C10 C8 I1 121.10(13) 2_656 . ?
C8 C9 C10 120.93(16) . . ?
C8 C9 Cl1 120.26(13) . . ?
C10 C9 Cl1 118.80(13) . . ?
C8 C10 C9 120.92(16) 2_656 . ?
C8 C10 Cl2 120.00(13) 2_656 . ?
C9 C10 Cl2 119.08(14) . . ?

_refine_diff_density_max         0.503
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_eb885270_a
_database_code_depnum_ccdc_archive 'CCDC 1955227'
loop_
_audit_author_name
_audit_author_address
'Daniel K. Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            
'Cocrystal 1,2,4,5-tetrachlorobenzene and 1,2-bis(4-pyridyl)ethyne'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 N2, C6 Cl4 I2'
_chemical_formula_sum            'C18 H8 Cl4 I2 N2'
_chemical_formula_weight         647.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   4.0502(2)
_cell_length_b                   11.1860(7)
_cell_length_c                   12.1964(7)
_cell_angle_alpha                111.4920(10)
_cell_angle_beta                 90.6710(10)
_cell_angle_gamma                97.3320(10)
_cell_volume                     508.92(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    4869
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      27.24

_exptl_crystal_description       cut
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.114
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.03
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_max          0.30
_exptl_absorpt_coefficient_mu    3.620
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.704
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS V2014(Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      270(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3660

_diffrn_reflns_number            6363
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.798
_diffrn_reflns_theta_max         27.239
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2278
_reflns_number_gt                2182
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'XSeed (Barbour, 2001)'
_computing_publication_material  'XSeed (Barbour, 2001)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0166P)²+0.1538P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2278
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0159
_refine_ls_R_factor_gt           0.0150
_refine_ls_wR_factor_ref         0.0361
_refine_ls_wR_factor_gt          0.0356
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.71479(3) 0.70971(2) 0.29431(2) 0.03049(5) Uani 1 1 d . . . . .
Cl1 Cl 0.40991(15) 0.74923(5) 0.55799(5) 0.04115(12) Uani 1 1 d . . . . .
N1 N 0.8744(5) 0.45411(16) 0.14797(17) 0.0409(4) Uani 1 1 d . . . . .
C1 C 0.8080(5) 0.24605(19) -0.00939(18) 0.0356(4) Uani 1 1 d . . . . .
H1 H 0.735449 0.195728 -0.087269 0.043 Uiso 1 1 calc R U . . .
Cl2 Cl 0.22016(14) 1.00214(5) 0.73728(4) 0.03989(12) Uani 1 1 d . . . . .
C2 C 0.7777(5) 0.3767(2) 0.0374(2) 0.0391(5) Uani 1 1 d . . . . .
H2 H 0.684212 0.412467 -0.011344 0.047 Uiso 1 1 calc R U . . .
C3 C 1.0110(6) 0.4012(2) 0.21596(19) 0.0420(5) Uani 1 1 d . . . . .
H3 H 1.081757 0.454326 0.293328 0.050 Uiso 1 1 calc R U . . .
C4 C 1.0536(6) 0.27191(19) 0.17808(18) 0.0381(5) Uani 1 1 d . . . . .
H4 H 1.150157 0.239258 0.228791 0.046 Uiso 1 1 calc R U . . .
C5 C 0.9488(5) 0.19154(17) 0.06222(17) 0.0296(4) Uani 1 1 d . . . . .
C6 C 0.9849(5) 0.05594(19) 0.01816(18) 0.0346(4) Uani 1 1 d . . . . .
C7 C 0.5883(4) 0.88351(17) 0.41738(15) 0.0251(3) Uani 1 1 d . . . . .
C8 C 0.4622(4) 0.88756(17) 0.52433(15) 0.0261(3) Uani 1 1 d . . . . .
C9 C 0.3750(4) 1.00233(17) 0.60599(15) 0.0257(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C7 2.1046(17) . ?
Cl1 C8 1.7296(18) . ?
N1 C2 1.329(3) . ?
N1 C3 1.333(3) . ?
C1 C2 1.383(3) . ?
C1 C5 1.388(3) . ?
Cl2 C9 1.7272(18) . ?
C3 C4 1.382(3) . ?
C4 C5 1.394(3) . ?
C5 C6 1.439(3) . ?
C6 C6 1.188(4) 2_755 ?
C7 C8 1.394(2) . ?
C7 C9 1.398(2) 2_676 ?
C8 C9 1.397(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C3 117.11(17) . . ?
C2 C1 C5 118.67(19) . . ?
N1 C2 C1 123.85(19) . . ?
N1 C3 C4 123.8(2) . . ?
C3 C4 C5 118.54(19) . . ?
C1 C5 C4 118.05(17) . . ?
C1 C5 C6 120.97(18) . . ?
C4 C5 C6 120.98(18) . . ?
C6 C6 C5 179.9(4) 2_755 . ?
C8 C7 C9 118.09(15) . 2_676 ?
C8 C7 I1 120.76(13) . . ?
C9 C7 I1 121.15(13) 2_676 . ?
C7 C8 C9 121.06(16) . . ?
C7 C8 Cl1 120.19(13) . . ?
C9 C8 Cl1 118.75(14) . . ?
C8 C9 C7 120.85(16) . 2_676 ?
C8 C9 Cl2 119.21(14) . . ?
C7 C9 Cl2 119.94(13) 2_676 . ?

_refine_diff_density_max         0.536
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_hut19_49_290
_database_code_depnum_ccdc_archive 'CCDC 1954983'
loop_
_audit_author_name
_audit_author_address
'Daniel K. Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-09-20 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_hut19_49_290        
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.840 Why?  
RESPONSE: The crystal diffraction quality of high angle data is greatly reduced
          at this temperature. 
;
_vrf_PLAT911_hut19_49_290        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        295 Report
RESPONSE: Due to the loss of high angle reflections at this temperature.
;
_vrf_PLAT088_hut19_49_290        
;
PROBLEM: Poor Data / Parameter Ratio ....................       9.30 Note  
RESPONSE: Due to the loss of high angle data.
;
# end Validation Reply Form

_audit_creation_date             2019-09-06T14:52:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H10 Cl4 I2 N2'
_chemical_formula_weight         649.88

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.08394(6)
_cell_length_b                   10.93443(15)
_cell_length_c                   12.37987(14)
_cell_angle_alpha                110.9256(12)
_cell_angle_beta                 92.4643(12)
_cell_angle_gamma                95.0316(12)
_cell_volume                     512.734(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    11298
_cell_measurement_theta_min      3.821
_cell_measurement_theta_max      76.844

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.048
_exptl_crystal_density_diffrn    2.105
_exptl_crystal_F_000             306
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -4 7 0.0254
0 7 -3 0.0206
-3 1 -1 0.0667
0 4 -8 0.0449
-3 0 0 0.0713
3 0 0 0.0225
0 -6 -2 0.0356
0 -4 -5 0.0281
0 -6 -1 0.0337
0 6 2 0.0131


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    28.929
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
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_correction_T_min  0.136
_exptl_absorpt_correction_T_max  0.449
_shelx_estimated_absorpt_T_min   0.129
_shelx_estimated_absorpt_T_max   0.337

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      290(2)
_diffrn_ambient_environment      air
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0152783
_diffrn_orient_matrix_ub_12      -0.0109926
_diffrn_orient_matrix_ub_13      -0.1277328
_diffrn_orient_matrix_ub_21      0.0302422
_diffrn_orient_matrix_ub_22      0.1513085
_diffrn_orient_matrix_ub_23      0.0392697
_diffrn_orient_matrix_ub_31      0.3783835
_diffrn_orient_matrix_ub_32      0.0042915
_diffrn_orient_matrix_ub_33      0.0024226
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_number            11096
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.835
_diffrn_reflns_theta_max         75.679
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.84
_diffrn_measured_fraction_theta_max 0.753
_diffrn_reflns_Laue_measured_fraction_full 0.84
_diffrn_reflns_Laue_measured_fraction_max 0.753
_diffrn_reflns_point_group_measured_fraction_full 0.84
_diffrn_reflns_point_group_measured_fraction_max 0.753
_reflns_Friedel_coverage         0
_reflns_number_total             1600
_reflns_number_gt                1507
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+0.1916P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0033(4)
_refine_ls_number_reflns         1600
_refine_ls_number_parameters     172
_refine_ls_number_restraints     343
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.077
_refine_ls_wR_factor_gt          0.0749
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      0.96
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.65
_refine_diff_density_min         -0.994
_refine_diff_density_rms         0.099

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


_refine_special_details          
;
 The 4,4'-vinylenedipyridine molecule is undergoing detectable pedal motion at
 this temperature. The major and minor positions of the disorder (A and B sites) 
 were allowed to refine their occupancies to a total value of 1. The A and B
 sites had occupancies of 0.87 and 0.13, respectively. To help model this 
 disorder and maintain reasonable ADP values SIMU, RIGU, DFIX and AFIX 
 restraints and constraints were applied.  
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.71461(6) 0.71086(3) 0.28892(2) 0.04590(18) Uani 1 1 d . . . . .
Cl1 Cl 0.4167(4) 0.73590(12) 0.54306(12) 0.0585(3) Uani 1 1 d . . . . .
Cl2 Cl 0.2350(3) 0.98868(13) 0.72805(10) 0.0546(3) Uani 1 1 d . . . . .
C1 C 0.5876(10) 0.8838(5) 0.4153(4) 0.0398(10) Uani 1 1 d . . . . .
C2 C 0.4661(10) 0.8820(4) 0.5180(4) 0.0369(9) Uani 1 1 d . . . . .
C3 C 0.3800(10) 0.9956(4) 0.6009(4) 0.0377(9) Uani 1 1 d . . . . .
N1A N 0.885(2) 0.4535(6) 0.1416(6) 0.0513(14) Uani 0.873(13) 1 d . U P A 1
C4A C 1.0420(19) 0.4078(7) 0.2147(6) 0.0518(16) Uani 0.873(13) 1 d . U P A 1
H4A H 1.109262 0.466225 0.289386 0.062 Uiso 0.873(13) 1 calc R U P A 1
C5A C 1.1084(17) 0.2790(7) 0.1846(6) 0.0492(14) Uani 0.873(13) 1 d . U P A 1
H5A H 1.221081 0.252556 0.23801 0.059 Uiso 0.873(13) 1 calc R U P A 1
C6A C 1.0071(18) 0.1892(6) 0.0750(7) 0.0415(13) Uani 0.873(13) 1 d D U P A 1
C7A C 0.8449(19) 0.2363(7) 0.0001(6) 0.0467(14) Uani 0.873(13) 1 d . U P A 1
H7A H 0.77101 0.179583 -0.074641 0.056 Uiso 0.873(13) 1 calc R U P A 1
C8A C 0.792(2) 0.3683(7) 0.0365(7) 0.0521(14) Uani 0.873(13) 1 d . U P A 1
H8A H 0.686427 0.397929 -0.015945 0.063 Uiso 0.873(13) 1 calc R U P A 1
C9A C 1.0723(16) 0.0507(5) 0.0436(6) 0.0431(15) Uani 0.873(13) 1 d D U P A 1
H9A H 1.23231 0.0336 0.090421 0.052 Uiso 0.873(13) 1 calc R U P A 1
N1B N 0.935(13) 0.453(3) 0.163(4) 0.050(3) Uani 0.127(13) 1 d G U P A 2
C4B C 1.082(11) 0.373(5) 0.213(3) 0.050(3) Uani 0.127(13) 1 d G U P A 2
H4B H 1.185418 0.410146 0.287606 0.06 Uiso 0.127(13) 1 calc R U P A 2
C5B C 1.075(10) 0.239(4) 0.151(4) 0.046(3) Uani 0.127(13) 1 d G U P A 2
H5B H 1.173209 0.185914 0.184351 0.056 Uiso 0.127(13) 1 calc R U P A 2
C6B C 0.921(11) 0.184(3) 0.040(4) 0.044(3) Uani 0.127(13) 1 d DG U P A 2
C7B C 0.774(10) 0.263(4) -0.010(3) 0.045(3) Uani 0.127(13) 1 d G U P A 2
H7B H 0.670274 0.226444 -0.084842 0.054 Uiso 0.127(13) 1 calc R U P A 2
C8B C 0.781(12) 0.398(4) 0.052(4) 0.049(3) Uani 0.127(13) 1 d G U P A 2
H8B H 0.68248 0.450676 0.018412 0.059 Uiso 0.127(13) 1 calc R U P A 2
C9B C 0.925(12) 0.039(3) -0.013(4) 0.042(4) Uani 0.127(13) 1 d D U P A 2
H9B H 0.781579 -0.00017 -0.079158 0.05 Uiso 0.127(13) 1 calc R U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 2.102(4) . ?
I1 N1A 2.919(6) . ?
I1 N1B 2.94(3) . ?
Cl1 C2 1.730(4) . ?
Cl2 C3 1.730(4) . ?
C1 C2 1.390(6) . ?
C1 C3 1.399(7) 2_676 ?
C2 C3 1.384(6) . ?
N1A C8A 1.317(8) . ?
N1A C4A 1.344(9) . ?
C4A C5A 1.378(9) . ?
C4A H4A 0.93 . ?
C5A C6A 1.380(9) . ?
C5A H5A 0.93 . ?
C6A C7A 1.383(8) . ?
C6A C9A 1.475(7) . ?
C7A C8A 1.389(9) . ?
C7A H7A 0.93 . ?
C8A H8A 0.93 . ?
C9A C9A 1.311(13) 2_755 ?
C9A H9A 0.93 . ?
N1B C4B 1.39 . ?
N1B C8B 1.39 . ?
C4B C5B 1.39 . ?
C4B H4B 0.93 . ?
C5B C6B 1.39 . ?
C5B H5B 0.93 . ?
C6B C7B 1.39 . ?
C6B C9B 1.48(3) . ?
C7B C8B 1.39 . ?
C7B H7B 0.93 . ?
C8B H8B 0.93 . ?
C9B C9B 1.22(9) 2_755 ?
C9B H9B 0.93 . ?

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
C1 I1 N1A 171.11(19) . . ?
C1 I1 N1B 165.7(11) . . ?
C2 C1 C3 117.5(4) . 2_676 ?
C2 C1 I1 121.0(3) . . ?
C3 C1 I1 121.5(3) 2_676 . ?
C3 C2 C1 121.1(4) . . ?
C3 C2 Cl1 119.0(3) . . ?
C1 C2 Cl1 120.0(3) . . ?
C2 C3 C1 121.4(4) . 2_676 ?
C2 C3 Cl2 119.3(3) . . ?
C1 C3 Cl2 119.3(3) 2_676 . ?
C8A N1A C4A 116.8(5) . . ?
C8A N1A I1 136.5(5) . . ?
C4A N1A I1 104.8(4) . . ?
N1A C4A C5A 123.5(6) . . ?
N1A C4A H4A 118.3 . . ?
C5A C4A H4A 118.3 . . ?
C4A C5A C6A 119.7(6) . . ?
C4A C5A H5A 120.1 . . ?
C6A C5A H5A 120.1 . . ?
C5A C6A C7A 116.8(5) . . ?
C5A C6A C9A 119.8(6) . . ?
C7A C6A C9A 123.5(6) . . ?
C6A C7A C8A 120.0(5) . . ?
C6A C7A H7A 120 . . ?
C8A C7A H7A 120 . . ?
N1A C8A C7A 123.2(6) . . ?
N1A C8A H8A 118.4 . . ?
C7A C8A H8A 118.4 . . ?
C9A C9A C6A 126.7(8) 2_755 . ?
C9A C9A H9A 116.7 2_755 . ?
C6A C9A H9A 116.7 . . ?
C4B N1B C8B 120 . . ?
C4B N1B I1 126(3) . . ?
C8B N1B I1 111(3) . . ?
N1B C4B C5B 120 . . ?
N1B C4B H4B 120 . . ?
C5B C4B H4B 120 . . ?
C6B C5B C4B 120 . . ?
C6B C5B H5B 120 . . ?
C4B C5B H5B 120 . . ?
C5B C6B C7B 120 . . ?
C5B C6B C9B 113(4) . . ?
C7B C6B C9B 127(4) . . ?
C8B C7B C6B 120 . . ?
C8B C7B H7B 120 . . ?
C6B C7B H7B 120 . . ?
C7B C8B N1B 120 . . ?
C7B C8B H8B 120 . . ?
N1B C8B H8B 120 . . ?
C9B C9B C6B 134(6) 2_755 . ?
C9B C9B H9B 113.1 2_755 . ?
C6B C9B H9B 113.1 . . ?

####################################################################### 
# 
# 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_eb888210_a
_database_code_depnum_ccdc_archive 'CCDC 1955224'
loop_
_audit_author_name
_audit_author_address
'Daniel K. Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            
'Cocrystal 1,2,4,5-tetrachlorobenzene and 1,2-bis(4-pyridyl)ethyne'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 N2, C6 Cl4 I2'
_chemical_formula_sum            'C18 H8 Cl4 I2 N2'
_chemical_formula_weight         647.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   4.0263(3)
_cell_length_b                   11.1831(9)
_cell_length_c                   12.1654(10)
_cell_angle_alpha                111.5010(10)
_cell_angle_beta                 90.5580(10)
_cell_angle_gamma                97.5490(10)
_cell_volume                     504.23(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    6488
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      33.03

_exptl_crystal_description       cut
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.134
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.03
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_max          0.30
_exptl_absorpt_coefficient_mu    3.654
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.703
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS V2014(Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      210(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3660

_diffrn_reflns_number            8319
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.803
_diffrn_reflns_theta_max         33.028
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3450
_reflns_number_gt                3197
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'XSeed (Barbour, 2001)'
_computing_publication_material  'XSeed (Barbour, 2001)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+0.7097P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3450
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0205
_refine_ls_wR_factor_ref         0.0482
_refine_ls_wR_factor_gt          0.0451
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_restrained_S_all      1.224
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.71500(4) 0.70927(2) 0.29377(2) 0.02480(4) Uani 1 1 d . . . . .
Cl1 Cl 0.40670(17) 0.74894(5) 0.55826(5) 0.03240(12) Uani 1 1 d . . . . .
N1 N 0.8744(6) 0.45463(19) 0.14803(19) 0.0320(4) Uani 1 1 d . . . . .
C1 C 0.8077(6) 0.2462(2) -0.0098(2) 0.0288(5) Uani 1 1 d . . . . .
H1 H 0.734973 0.195091 -0.088814 0.035 Uiso 1 1 calc R U . . .
Cl2 Cl 0.21658(16) 1.00228(6) 0.73801(5) 0.03146(12) Uani 1 1 d . . . . .
C2 C 0.7768(6) 0.3768(2) 0.0366(2) 0.0310(5) Uani 1 1 d . . . . .
H2 H 0.681903 0.412760 -0.012923 0.037 Uiso 1 1 calc R U . . .
C3 C 1.0105(7) 0.4019(2) 0.2166(2) 0.0326(5) Uani 1 1 d . . . . .
H3 H 1.081522 0.455710 0.295039 0.039 Uiso 1 1 calc R U . . .
C4 C 1.0533(7) 0.2721(2) 0.1787(2) 0.0303(5) Uani 1 1 d . . . . .
H4 H 1.150547 0.239055 0.230112 0.036 Uiso 1 1 calc R U . . .
C5 C 0.9484(6) 0.1919(2) 0.0624(2) 0.0246(4) Uani 1 1 d . . . . .
C6 C 0.9850(6) 0.0564(2) 0.0184(2) 0.0273(4) Uani 1 1 d . . . . .
C7 C 0.5886(5) 0.88325(19) 0.41691(17) 0.0197(4) Uani 1 1 d . . . . .
C8 C 0.4603(5) 0.8872(2) 0.52450(18) 0.0214(4) Uani 1 1 d . . . . .
C9 C 0.3730(5) 1.0025(2) 0.60641(18) 0.0216(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C7 2.1042(19) . ?
Cl1 C8 1.728(2) . ?
N1 C3 1.334(3) . ?
N1 C2 1.336(3) . ?
C1 C2 1.382(3) . ?
C1 C5 1.391(3) . ?
Cl2 C9 1.727(2) . ?
C3 C4 1.388(3) . ?
C4 C5 1.393(3) . ?
C5 C6 1.439(3) . ?
C6 C6 1.196(4) 2_755 ?
C7 C9 1.397(3) 2_676 ?
C7 C8 1.399(3) . ?
C8 C9 1.401(3) . ?

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 117.3(2) . . ?
C2 C1 C5 118.8(2) . . ?
N1 C2 C1 123.5(2) . . ?
N1 C3 C4 123.8(2) . . ?
C3 C4 C5 118.3(2) . . ?
C1 C5 C4 118.3(2) . . ?
C1 C5 C6 120.9(2) . . ?
C4 C5 C6 120.8(2) . . ?
C6 C6 C5 179.8(4) 2_755 . ?
C9 C7 C8 118.10(18) 2_676 . ?
C9 C7 I1 121.26(15) 2_676 . ?
C8 C7 I1 120.64(15) . . ?
C7 C8 C9 120.90(19) . . ?
C7 C8 Cl1 120.23(16) . . ?
C9 C8 Cl1 118.88(17) . . ?
C7 C9 C8 121.00(19) 2_676 . ?
C7 C9 Cl2 119.91(16) 2_676 . ?
C8 C9 Cl2 119.08(17) . . ?

_refine_diff_density_max         1.129
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.117

####################################################################### 
# 
# 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_eb887230_a
_database_code_depnum_ccdc_archive 'CCDC 1955225'
loop_
_audit_author_name
_audit_author_address
'Daniel K. Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            
'Cocrystal 1,2,4,5-tetrachlorobenzene and 1,2-bis(4-pyridyl)ethyne'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 N2, C6 Cl4 I2'
_chemical_formula_sum            'C18 H8 Cl4 I2 N2'
_chemical_formula_weight         647.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   4.0336(2)
_cell_length_b                   11.1825(7)
_cell_length_c                   12.1732(7)
_cell_angle_alpha                111.4960(10)
_cell_angle_beta                 90.5990(10)
_cell_angle_gamma                97.4800(10)
_cell_volume                     505.53(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    5088
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      27.29

_exptl_crystal_description       cut
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.128
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.03
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_max          0.30
_exptl_absorpt_coefficient_mu    3.644
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.702
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS V2014(Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      230(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3660

_diffrn_reflns_number            6384
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.125
_diffrn_reflns_theta_max         27.287
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2271
_reflns_number_gt                2201
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'XSeed (Barbour, 2001)'
_computing_publication_material  'XSeed (Barbour, 2001)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0163P)²+0.1476P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2271
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0148
_refine_ls_R_factor_gt           0.0141
_refine_ls_wR_factor_ref         0.0339
_refine_ls_wR_factor_gt          0.0335
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.28506(3) 0.29058(2) 0.70605(2) 0.02514(4) Uani 1 1 d . . . . .
Cl1 Cl 0.59245(13) 0.25099(4) 0.44183(4) 0.03436(11) Uani 1 1 d . . . . .
N1 N 0.1254(4) 0.54555(15) 0.85208(15) 0.0342(4) Uani 1 1 d . . . . .
C1 C 0.1927(5) 0.75385(18) 1.00977(17) 0.0300(4) Uani 1 1 d . . . . .
H1 H 0.265948 0.804809 1.088669 0.036 Uiso 1 1 calc R U . . .
Cl2 Cl 0.78236(13) -0.00216(4) 0.26223(4) 0.03305(10) Uani 1 1 d . . . . .
C2 C 0.2230(5) 0.62322(18) 0.96295(18) 0.0328(4) Uani 1 1 d . . . . .
H2 H 0.318119 0.587157 1.012297 0.039 Uiso 1 1 calc R U . . .
C3 C -0.0110(5) 0.59852(19) 0.78366(17) 0.0353(4) Uani 1 1 d . . . . .
H3 H -0.082367 0.544737 0.705284 0.042 Uiso 1 1 calc R U . . .
C4 C -0.0532(5) 0.72777(18) 0.82143(17) 0.0317(4) Uani 1 1 d . . . . .
H4 H -0.150290 0.760676 0.769912 0.038 Uiso 1 1 calc R U . . .
C5 C 0.0514(4) 0.80843(16) 0.93763(16) 0.0249(3) Uani 1 1 d . . . . .
C6 C 0.0145(5) 0.94388(18) 0.98164(16) 0.0287(4) Uani 1 1 d . . . . .
C7 C 0.4111(4) 0.11652(16) 0.58284(14) 0.0212(3) Uani 1 1 d . . . . .
C8 C 0.5394(4) 0.11267(16) 0.47540(14) 0.0219(3) Uani 1 1 d . . . . .
C9 C 0.6265(4) -0.00243(16) 0.39386(14) 0.0219(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C7 2.1048(16) . ?
Cl1 C8 1.7275(17) . ?
N1 C2 1.331(3) . ?
N1 C3 1.336(3) . ?
C1 C2 1.383(3) . ?
C1 C5 1.393(3) . ?
Cl2 C9 1.7284(17) . ?
C3 C4 1.381(3) . ?
C4 C5 1.395(3) . ?
C5 C6 1.438(2) . ?
C6 C6 1.190(4) 2_577 ?
C7 C9 1.395(2) 2_656 ?
C7 C8 1.400(2) . ?
C8 C9 1.398(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C3 117.14(16) . . ?
C2 C1 C5 118.65(17) . . ?
N1 C2 C1 123.83(18) . . ?
N1 C3 C4 123.79(18) . . ?
C3 C4 C5 118.59(17) . . ?
C1 C5 C4 118.00(16) . . ?
C1 C5 C6 121.01(17) . . ?
C4 C5 C6 120.99(16) . . ?
C6 C6 C5 179.7(3) 2_577 . ?
C9 C7 C8 118.10(15) 2_656 . ?
C9 C7 I1 121.26(12) 2_656 . ?
C8 C7 I1 120.63(12) . . ?
C9 C8 C7 120.80(15) . . ?
C9 C8 Cl1 119.02(13) . . ?
C7 C8 Cl1 120.19(13) . . ?
C7 C9 C8 121.11(15) 2_656 . ?
C7 C9 Cl2 119.92(13) 2_656 . ?
C8 C9 Cl2 118.97(13) . . ?

_refine_diff_density_max         0.531
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_hut19_48_250
_database_code_depnum_ccdc_archive 'CCDC 1954975'
loop_
_audit_author_name
_audit_author_address
'Daniel K. Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-09-20 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT250_hut19_48_250        
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.9 Note  
RESPONSE: Due to the pedal motion of molecules within the structure.
;
_vrf_PLAT431_hut19_48_250        
;
PROBLEM: Short Inter HL..A Contact  Cl1      ..N2B      .       3.13 Ang.  
RESPONSE: A feature of the structure.
;
_vrf_PLAT911_hut19_48_250        
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          9 Report
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2019-09-05T11:52:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C16 H8 Cl4 I2 N4'
_chemical_formula_weight         651.86

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.04169(16)
_cell_length_b                   10.8302(3)
_cell_length_c                   12.3901(3)
_cell_angle_alpha                111.496(3)
_cell_angle_beta                 92.077(3)
_cell_angle_gamma                94.678(3)
_cell_volume                     501.66(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    9578
_cell_measurement_theta_min      3.867
_cell_measurement_theta_max      76.725

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.054
_exptl_crystal_density_diffrn    2.158
_exptl_crystal_F_000             306
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 6 1 0.0747
2 3 -2 0.0542
3 0 1 0.0594
0 -6 -1 0.0462
0 -4 8 0.0381
-3 0 -1 0.0276
0 7 -3 0.0515
0 4 -8 0.0132
1 3 5 0.062
0 -5 7 0.0339
0 1 -8 0.0283
2 4 2 0.0644


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    29.601
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.58a (Rigaku Oxford Diffraction, 2019)
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_correction_T_min  0.068
_exptl_absorpt_correction_T_max  0.472
_shelx_estimated_absorpt_T_min   0.101
_shelx_estimated_absorpt_T_max   0.298

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_ambient_temperature      250(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.1503321
_diffrn_orient_matrix_ub_12      0.1446575
_diffrn_orient_matrix_ub_13      0.0679349
_diffrn_orient_matrix_ub_21      0.0579524
_diffrn_orient_matrix_ub_22      0.0188035
_diffrn_orient_matrix_ub_23      -0.1154726
_diffrn_orient_matrix_ub_31      -0.3479241
_diffrn_orient_matrix_ub_32      0.0483621
_diffrn_orient_matrix_ub_33      -0.0004097
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0799
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_number            16382
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.844
_diffrn_reflns_theta_max         77.141
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.957
_reflns_Friedel_coverage         0
_reflns_number_total             2024
_reflns_number_gt                1925
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0551P)²+0.8922P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2024
_refine_ls_number_parameters     159
_refine_ls_number_restraints     343
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.156
_refine_diff_density_min         -1.332
_refine_diff_density_rms         0.158

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 The 4,4'-azopyridine molecule is undergoing detectable pedal motion at
 this temperature. The major and minor positions of the disorder (A and B sites)  
 were allowed to refine their occupancies to a total value of 1. The A and B
 sites had occupancies of 0.55 and 0.45, respectively. To help model this 
 disorder and maintain reasonable ADP values SIMU, RIGU, DFIX and AFIX 
 restraints and constraints were applied. During the final refinements the 
 inconsistent reflections 2 9 3, 4 -8 6, 0 12 0, -3 10 1, and -4 5 0 were 
 omitted. 
;


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.77242(7) 0.29489(3) 0.20940(2) 0.04035(14) Uani 1 1 d . . . . .
Cl1 Cl 0.7175(4) -0.00702(13) 0.22798(10) 0.0478(3) Uani 1 1 d . . . . .
Cl2 Cl 0.9201(4) -0.26447(12) 0.04606(11) 0.0509(3) Uani 1 1 d . . . . .
C1 C 0.9091(12) 0.1185(4) 0.0841(4) 0.0346(9) Uani 1 1 d . . . . .
C2 C 0.8742(12) -0.0021(5) 0.1023(4) 0.0347(9) Uani 1 1 d . . . . .
C3 C 0.9666(12) -0.1182(4) 0.0189(4) 0.0354(9) Uani 1 1 d . . . . .
N1A N 0.606(4) 0.5577(6) 0.3669(9) 0.0432(18) Uani 0.546(15) 1 d G U P A 1
C4A C 0.442(3) 0.5988(8) 0.2874(7) 0.0425(18) Uani 0.546(15) 1 d G U P A 1
H4A H 0.366545 0.536483 0.213231 0.051 Uiso 0.546(15) 1 calc R U P A 1
C5A C 0.388(3) 0.7322(10) 0.3175(8) 0.0435(19) Uani 0.546(15) 1 d G U P A 1
H5A H 0.277326 0.759966 0.263679 0.052 Uiso 0.546(15) 1 calc R U P A 1
C6A C 0.500(3) 0.8244(6) 0.4271(9) 0.0402(18) Uani 0.546(15) 1 d DG U P A 1
C7A C 0.664(3) 0.7833(8) 0.5066(7) 0.0396(19) Uani 0.546(15) 1 d G U P A 1
H7A H 0.739043 0.845655 0.580698 0.048 Uiso 0.546(15) 1 calc R U P A 1
C8A C 0.717(3) 0.6500(9) 0.4765(8) 0.0435(19) Uani 0.546(15) 1 d G U P A 1
H8A H 0.828265 0.622172 0.530253 0.052 Uiso 0.546(15) 1 calc R U P A 1
N2A N 0.444(2) 0.9613(10) 0.4510(9) 0.043(2) Uani 0.546(15) 1 d D U P A 1
N1B N 0.573(5) 0.5561(7) 0.3510(12) 0.048(2) Uani 0.454(15) 1 d G U P A 2
C4B C 0.433(4) 0.6298(12) 0.2932(8) 0.050(2) Uani 0.454(15) 1 d G U P A 2
H4B H 0.346784 0.587404 0.215621 0.06 Uiso 0.454(15) 1 calc R U P A 2
C5B C 0.422(4) 0.7662(11) 0.3502(11) 0.044(2) Uani 0.454(15) 1 d G U P A 2
H5B H 0.32724 0.816042 0.311069 0.053 Uiso 0.454(15) 1 calc R U P A 2
C6B C 0.550(3) 0.8289(7) 0.4649(11) 0.041(2) Uani 0.454(15) 1 d DG U P A 2
C7B C 0.689(4) 0.7552(11) 0.5227(8) 0.043(2) Uani 0.454(15) 1 d G U P A 2
H7B H 0.775848 0.797588 0.600347 0.052 Uiso 0.454(15) 1 calc R U P A 2
C8B C 0.701(4) 0.6188(11) 0.4658(11) 0.044(2) Uani 0.454(15) 1 d G U P A 2
H8B H 0.795394 0.56895 0.5049 0.053 Uiso 0.454(15) 1 calc R U P A 2
N2B N 0.546(3) 0.9704(12) 0.5288(10) 0.045(2) Uani 0.454(15) 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 2.104(5) . ?
I1 N1B 2.927(9) . ?
I1 N1A 2.950(7) . ?
Cl1 C2 1.719(5) . ?
Cl2 C3 1.734(5) . ?
C1 C3 1.388(7) 2_755 ?
C1 C2 1.401(7) . ?
C2 C3 1.393(7) . ?
N1A C4A 1.39 . ?
N1A C8A 1.39 . ?
C4A C5A 1.39 . ?
C4A H4A 0.94 . ?
C5A C6A 1.39 . ?
C5A H5A 0.94 . ?
C6A C7A 1.39 . ?
C6A N2A 1.441(10) . ?
C7A C8A 1.39 . ?
C7A H7A 0.94 . ?
C8A H8A 0.94 . ?
N2A N2A 1.24(2) 2_676 ?
N1B C4B 1.39 . ?
N1B C8B 1.39 . ?
C4B C5B 1.39 . ?
C4B H4B 0.94 . ?
C5B C6B 1.39 . ?
C5B H5B 0.94 . ?
C6B C7B 1.39 . ?
C6B N2B 1.446(12) . ?
C7B C8B 1.39 . ?
C7B H7B 0.94 . ?
C8B H8B 0.94 . ?
N2B N2B 1.19(3) 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
C1 I1 N1B 170.3(3) . . ?
C1 I1 N1A 173.4(3) . . ?
C3 C1 C2 118.3(4) 2_755 . ?
C3 C1 I1 121.0(3) 2_755 . ?
C2 C1 I1 120.7(3) . . ?
C3 C2 C1 120.2(4) . . ?
C3 C2 Cl1 119.8(4) . . ?
C1 C2 Cl1 120.0(4) . . ?
C1 C3 C2 121.5(4) 2_755 . ?
C1 C3 Cl2 120.2(4) 2_755 . ?
C2 C3 Cl2 118.4(4) . . ?
C4A N1A C8A 120 . . ?
C4A N1A I1 99.9(5) . . ?
C8A N1A I1 137.3(5) . . ?
C5A C4A N1A 120 . . ?
C5A C4A H4A 120 . . ?
N1A C4A H4A 120 . . ?
C6A C5A C4A 120 . . ?
C6A C5A H5A 120 . . ?
C4A C5A H5A 120 . . ?
C5A C6A C7A 120 . . ?
C5A C6A N2A 116.9(7) . . ?
C7A C6A N2A 123.1(7) . . ?
C6A C7A C8A 120 . . ?
C6A C7A H7A 120 . . ?
C8A C7A H7A 120 . . ?
C7A C8A N1A 120 . . ?
C7A C8A H8A 120 . . ?
N1A C8A H8A 120 . . ?
N2A N2A C6A 113.6(11) 2_676 . ?
C4B N1B C8B 120 . . ?
C4B N1B I1 117.6(7) . . ?
C8B N1B I1 119.8(7) . . ?
C5B C4B N1B 120 . . ?
C5B C4B H4B 120 . . ?
N1B C4B H4B 120 . . ?
C6B C5B C4B 120 . . ?
C6B C5B H5B 120 . . ?
C4B C5B H5B 120 . . ?
C5B C6B C7B 120 . . ?
C5B C6B N2B 122.7(9) . . ?
C7B C6B N2B 117.3(9) . . ?
C6B C7B C8B 120 . . ?
C6B C7B H7B 120 . . ?
C8B C7B H7B 120 . . ?
C7B C8B N1B 120 . . ?
C7B C8B H8B 120 . . ?
N1B C8B H8B 120 . . ?
N2B N2B C6B 113.9(15) 2_676 . ?
