# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_clp
_database_code_depnum_ccdc_archive 'CCDC 1483082'
_audit_update_record             
;
2016-06-01 deposited with the CCDC.
2016-08-09 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT155_clp                 
;
PROBLEM: The Triclinic Unitcell is NOT Reduced ..........     Please Do !
RESPONSE: A reduced triclinic cell with the same a, b and c parameteres but different angles was found. Nevertheless for this alternative cell  the Rmerge value was to big. With the original cell the Rmerge value is more reasonable.
;
_vrf_PLAT242_clp                 
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         C9 Check
RESPONSE: This alerts are probably the consequence of positional disorder caused by crystal decomposition.
;
_vrf_PLAT250_clp                 
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.9 Note
RESPONSE: This alerts are probably the consequence of positional disorder caused by crystal decomposition.
;
_vrf_PLAT334_clp                 
;
PROBLEM: Small Average Benzene  C-C Dist. C9     -C11_a         1.37 Ang.
RESPONSE: This alerts are probably the consequence of positional disorder caused by crystal decomposition.
;
_vrf_PLAT340_clp                 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00777 Ang.
RESPONSE: This alerts are probably the consequence of positional disorder caused by crystal decomposition. Considering that our work is essentially theoretical it was not necessary to get accurate atomic positions.
;
# Added during the CSD deposition process: Thursday 02 June 2016 12:22 AM
# end Validation Reply Form


_audit_creation_date             2016-05-31T04:01:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C22 H10 Cl6'
_chemical_formula_weight         487.03
_chemical_formula_moiety         'C16 H10, C6 Cl6'

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

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.367(3)
_cell_length_b                   8.555(2)
_cell_length_c                   15.803(5)
_cell_angle_alpha                94.02(2)
_cell_angle_beta                 102.77(3)
_cell_angle_gamma                89.86(3)
_cell_volume                     968.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    240(2)
_cell_measurement_reflns_used    1430
_cell_measurement_theta_min      3.4315
_cell_measurement_theta_max      29.6608
_cell_special_details            
;
A reduced triclinic cell with the same a, b and c parameteres
but different angles was found. Nevertheless for this alternative cell 
the Rmerge value was to big. With the original cell the Rmerge value
is more reasonable.
;



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

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4354
_exptl_crystal_size_mid          0.1846
_exptl_crystal_size_min          0.1206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_F_000             488
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist

-1 8 -15 0.0923
1 -8 15 0.0923
10 0 5 0.1996
-10 0 -5 0.1996
-1 -9 -17 0.0603
1 9 17 0.0603
0 12 -5 0.0801

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

_exptl_absorpt_coefficient_mu    0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS, TWINABS: Bruker (2001). Program name. Bruker AXS Inc., Madison,
Wisconsin, USA. or Sheldrick, G. M. (1996). Program name. University of
Göttingen, Germany.
;
_exptl_absorpt_correction_T_min  0.7599
_exptl_absorpt_correction_T_max  0.8759

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

_diffrn_ambient_temperature      240(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.4685
_diffrn_orient_matrix_ub_11      -0.0015174
_diffrn_orient_matrix_ub_12      -0.0684754
_diffrn_orient_matrix_ub_13      -0.0282018
_diffrn_orient_matrix_ub_21      0.016138
_diffrn_orient_matrix_ub_22      -0.0464826
_diffrn_orient_matrix_ub_23      0.0363095
_diffrn_orient_matrix_ub_31      -0.0973946
_diffrn_orient_matrix_ub_32      -0.0077613
_diffrn_orient_matrix_ub_33      -0.0039006
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.1075
_diffrn_reflns_number            6702
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.438
_diffrn_reflns_theta_max         25.253
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_number_total             3494
_reflns_number_gt                2616
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis 2007)'

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom
#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0698P)²+1.5333P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3494
_refine_ls_number_parameters     253
_refine_ls_number_restraints     249
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0663
_refine_ls_wR_factor_ref         0.1847
_refine_ls_wR_factor_gt          0.1674
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.745
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.778
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.084
_refine_special_details          
;
Most of the other alerts are consequence of
positional disorder caused by crystal decomposition.
Considering that our work is essentially theoretical it was
not necesary to get accurate atomic positions.
;
#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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 0.1484 0.1585 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl9 Cl 1.0393(2) 1.0474(2) 0.19914(9) 0.0760(5) Uani 1 d . .
Cl10 Cl 0.9247(2) 0.72069(18) 0.10417(12) 0.0732(5) Uani 1 d . .
Cl11 Cl 0.9061(2) 0.66883(17) -0.09324(12) 0.0753(5) Uani 1 d . .
Cl20 Cl 0.4769(2) 0.84225(15) 0.57596(9) 0.0595(4) Uani 1 d . .
Cl21 Cl 0.33033(18) 0.75784(16) 0.37917(9) 0.0552(4) Uani 1 d . .
Cl22 Cl 0.3690(2) 0.41744(17) 0.30225(8) 0.0584(4) Uani 1 d . .
C1 C 0.4047(6) 0.7067(8) 0.1285(5) 0.082(2) Uani 1 d . .
H1 H 0.3793 0.6294 0.163 0.099 Uiso 1 calc . .
C2 C 0.3904(5) 0.6709(7) 0.0421(5) 0.0729(17) Uani 1 d . .
H2 H 0.3556 0.5701 0.0181 0.087 Uiso 1 calc . .
C3 C 0.4282(4) 0.7866(6) -0.0114(3) 0.0518(12) Uani 1 d . .
C4 C 0.4808(5) 0.9390(5) 0.0261(3) 0.0374(10) Uani 1 d . .
C5 C 0.4956(5) 0.9751(6) 0.1168(3) 0.0503(12) Uani 1 d . .
C6 C 0.4557(6) 0.8539(8) 0.1660(4) 0.0712(17) Uani 1 d . .
H6 H 0.4641 0.8743 0.2254 0.085 Uiso 1 calc . .
C7 C 0.4157(6) 0.7571(7) -0.1028(4) 0.0656(15) Uani 1 d . .
H7 H 0.3819 0.6574 -0.1288 0.079 Uiso 1 calc . .
C8 C 0.5485(6) 1.1305(8) 0.1514(4) 0.0644(15) Uani 1 d . .
H8 H 0.5586 1.1548 0.2106 0.077 Uiso 1 calc . .
C9 C 1.0151(5) 1.0184(6) 0.0861(3) 0.0428(11) Uani 1 d . .
C10 C 0.9686(3) 0.8701(5) 0.0482(3) 0.0452(11) Uani 1 d . .
C11 C 0.9585(5) 0.8574(5) -0.0398(3) 0.0448(11) Uani 1 d . .
C12 C 0.8114(6) 0.7862(8) 0.3614(4) 0.0746(17) Uani 1 d . .
H12 H 0.7616 0.8626 0.3242 0.09 Uiso 1 calc . .
C13 C 0.8308(5) 0.6370(8) 0.3275(4) 0.0646(15) Uani 1 d . .
H13 H 0.7936 0.6136 0.2678 0.078 Uiso 1 calc . .
C14 C 0.9055(4) 0.5192(6) 0.3814(3) 0.0515(12) Uani 1 d . .
C15 C 0.9605(5) 0.5587(5) 0.4713(3) 0.0420(10) Uani 1 d . .
C16 C 0.9396(5) 0.7129(6) 0.5054(3) 0.0511(12) Uani 1 d . .
C17 C 0.8637(6) 0.8250(7) 0.4483(4) 0.0654(15) Uani 1 d . .
H17 H 0.8486 0.927 0.4699 0.078 Uiso 1 calc . .
C18 C 0.9286(7) 0.3613(7) 0.3497(4) 0.0624(15) Uani 1 d . .
H18 H 0.8908 0.3343 0.2903 0.075 Uiso 1 calc . .
C19 C 0.9969(7) 0.7491(7) 0.5972(4) 0.0607(14) Uani 1 d . .
H19 H 0.9824 0.8502 0.6204 0.073 Uiso 1 calc . .
C20 C 0.4867(6) 0.6525(5) 0.5339(3) 0.0407(11) Uani 1 d . .
C21 C 0.4257(6) 0.6156(6) 0.4458(3) 0.0408(10) Uani 1 d . .
C22 C 0.4404(6) 0.4634(6) 0.4113(3) 0.0400(10) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   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
Cl9 C9 1.755(5) . ?
Cl10 C10 1.676(5) . ?
Cl11 C11 1.770(5) . ?
Cl20 C20 1.718(5) . ?
Cl21 C21 1.713(5) . ?
Cl22 C22 1.705(5) . ?
C1 C2 1.360(8) . ?
C1 C6 1.371(8) . ?
C1 H1 0.93 . ?
C2 C3 1.413(7) . ?
C2 H2 0.93 . ?
C3 C4 1.412(6) . ?
C3 C7 1.430(7) . ?
C4 C5 1.424(6) . ?
C4 C4 1.442(8) 2_675 ?
C5 C6 1.408(7) . ?
C5 C8 1.423(7) . ?
C6 H6 0.93 . ?
C7 C8 1.334(9) 2_675 ?
C7 H7 0.93 . ?
C8 C7 1.334(9) 2_675 ?
C8 H8 0.93 . ?
C9 C11 1.369(7) 2_775 ?
C9 C10 1.375(6) . ?
C10 C11 1.373(6) . ?
C11 C9 1.369(7) 2_775 ?
C12 C17 1.360(8) . ?
C12 C13 1.369(8) . ?
C12 H12 0.93 . ?
C13 C14 1.398(7) . ?
C13 H13 0.93 . ?
C14 C15 1.406(6) . ?
C14 C18 1.430(7) . ?
C15 C16 1.411(6) . ?
C15 C15 1.436(9) 2_766 ?
C16 C17 1.394(7) . ?
C16 C19 1.431(7) . ?
C17 H17 0.93 . ?
C18 C19 1.343(8) 2_766 ?
C18 H18 0.93 . ?
C19 C18 1.343(8) 2_766 ?
C19 H19 0.93 . ?
C20 C21 1.378(6) . ?
C20 C22 1.390(6) 2_666 ?
C21 C22 1.390(7) . ?
C22 C20 1.390(6) 2_666 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.5(6) . . ?
C2 C1 H1 119.2 . . ?
C6 C1 H1 119.2 . . ?
C1 C2 C3 120.1(6) . . ?
C1 C2 H2 120 . . ?
C3 C2 H2 120 . . ?
C4 C3 C2 119.1(5) . . ?
C4 C3 C7 117.9(5) . . ?
C2 C3 C7 123.0(5) . . ?
C3 C4 C5 120.3(4) . . ?
C3 C4 C4 121.0(5) . 2_675 ?
C5 C4 C4 118.7(5) . 2_675 ?
C6 C5 C8 124.4(5) . . ?
C6 C5 C4 117.4(5) . . ?
C8 C5 C4 118.2(5) . . ?
C1 C6 C5 121.5(6) . . ?
C1 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C8 C7 C3 121.4(5) 2_675 . ?
C8 C7 H7 119.3 2_675 . ?
C3 C7 H7 119.3 . . ?
C7 C8 C5 122.9(5) 2_675 . ?
C7 C8 H8 118.6 2_675 . ?
C5 C8 H8 118.6 . . ?
C11 C9 C10 123.1(4) 2_775 . ?
C11 C9 Cl9 119.3(4) 2_775 . ?
C10 C9 Cl9 117.7(4) . . ?
C11 C10 C9 113.5(4) . . ?
C11 C10 Cl10 123.5(4) . . ?
C9 C10 Cl10 122.9(4) . . ?
C9 C11 C10 123.3(4) 2_775 . ?
C9 C11 Cl11 120.2(4) 2_775 . ?
C10 C11 Cl11 116.4(4) . . ?
C17 C12 C13 121.3(6) . . ?
C17 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C14 121.0(5) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C15 118.0(5) . . ?
C13 C14 C18 123.4(5) . . ?
C15 C14 C18 118.6(5) . . ?
C14 C15 C16 120.5(4) . . ?
C14 C15 C15 119.7(5) . 2_766 ?
C16 C15 C15 119.8(5) . 2_766 ?
C17 C16 C15 118.7(5) . . ?
C17 C16 C19 122.2(5) . . ?
C15 C16 C19 119.1(5) . . ?
C12 C17 C16 120.5(6) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C14 122.2(5) 2_766 . ?
C19 C18 H18 118.9 2_766 . ?
C14 C18 H18 118.9 . . ?
C18 C19 C16 120.6(5) 2_766 . ?
C18 C19 H19 119.7 2_766 . ?
C16 C19 H19 119.7 . . ?
C21 C20 C22 120.1(4) . 2_666 ?
C21 C20 Cl20 120.2(4) . . ?
C22 C20 Cl20 119.8(4) 2_666 . ?
C20 C21 C22 120.2(4) . . ?
C20 C21 Cl21 119.8(4) . . ?
C22 C21 Cl21 120.1(4) . . ?
C21 C22 C20 119.8(4) . 2_666 ?
C21 C22 Cl22 120.5(4) . . ?
C20 C22 Cl22 119.7(4) 2_666 . ?


# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_chemical_name_systematic        'Hexachlorobenzene-pyrene adduct'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method ethylether
####################################################################### 
# 
# 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_clt
_database_code_depnum_ccdc_archive 'CCDC 1483083'
_audit_update_record             
;
2016-06-01 deposited with the CCDC.
2016-08-09 downloaded from the CCDC.
;

_audit_creation_date             2016-05-31T04:04:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C24 H12 Cl6'
_chemical_formula_weight         513.04
_chemical_formula_moiety         'C18 H12, C6 Cl6'

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

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

_cell_length_a                   17.2096(3)
_cell_length_b                   7.28950(10)
_cell_length_c                   18.0874(3)
_cell_angle_alpha                90
_cell_angle_beta                 116.651(2)
_cell_angle_gamma                90
_cell_volume                     2027.98(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    107434
_cell_measurement_theta_min      3.3994
_cell_measurement_theta_max      54.4444

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5049
_exptl_crystal_size_mid          0.1458
_exptl_crystal_size_min          0.0772
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.68
_exptl_crystal_F_000             1032
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
24 0 -13 0.0729
-24 0 13 0.0729
1 10 -3 0.2426
-1 -10 3 0.2426
2 0 22 0.0386
-2 0 -22 0.0386


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

_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS, TWINABS: Bruker (2001). Program name. Bruker AXS Inc., Madison,
Wisconsin, USA. or Sheldrick, G. M. (1996). Program name. University of
Göttingen, Germany.
;
_exptl_absorpt_correction_T_min  0.8676
_exptl_absorpt_correction_T_max  0.9265

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.4685
_diffrn_orient_matrix_ub_11      -0.0322306
_diffrn_orient_matrix_ub_12      -0.0129626
_diffrn_orient_matrix_ub_13      -0.0413377
_diffrn_orient_matrix_ub_21      -0.0318336
_diffrn_orient_matrix_ub_22      -0.0130151
_diffrn_orient_matrix_ub_23      0.0143066
_diffrn_orient_matrix_ub_31      -0.0087019
_diffrn_orient_matrix_ub_32      0.0954939
_diffrn_orient_matrix_ub_33      -0.0036447
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.1222
_diffrn_reflns_number            436714
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.557
_diffrn_reflns_theta_max         30.438
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_number_total             6156
_reflns_number_gt                5536
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_special_details          
;
The missing reflections below Theta-Min could be a consecuence 
of the relatively large size of the unit-cell.
;

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

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis 2007)'

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#
_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom
#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0297P)²+1.2514P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6156
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0711
_refine_ls_wR_factor_gt          0.0661
_refine_ls_goodness_of_fit_ref   1.15
_refine_ls_restrained_S_all      1.15
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.065
_refine_special_details          
;
It has been observed that the central ring of triphenylene is not
fully aromatic.This explains the large averge C6-ring distances. 
Since there are strong intermolecular interactions between the
hexachlorobenzene and the triphenylene molecules so that the
centres of gravity are not in the unit-cell bounds.
Positive residual density on C-C bonds are found probably because of the
good quality of the obtained data set.
;
#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 '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 0.1484 0.1585 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.35904(8) 0.02503(17) 0.16546(7) 0.0181(2) Uani 1 d . .
H1 H 0.3276 0.0705 0.1934 0.022 Uiso 1 calc . .
C2 C 0.44572(8) -0.01779(19) 0.21068(7) 0.0208(2) Uani 1 d . .
H2 H 0.4735 -0.0018 0.269 0.025 Uiso 1 calc . .
C3 C 0.49258(8) -0.08475(18) 0.17043(8) 0.0195(2) Uani 1 d . .
H3 H 0.5524 -0.1145 0.2014 0.023 Uiso 1 calc . .
C4 C 0.45225(7) -0.10774(17) 0.08592(7) 0.0165(2) Uani 1 d . .
H4 H 0.4848 -0.1532 0.0591 0.02 Uiso 1 calc . .
C5 C 0.36657(8) -0.15534(16) -0.09402(7) 0.0162(2) Uani 1 d . .
H5 H 0.427 -0.18 -0.0639 0.019 Uiso 1 calc . .
C6 C 0.32602(8) -0.18278(17) -0.17827(7) 0.0188(2) Uani 1 d . .
H6 H 0.3585 -0.2254 -0.2057 0.023 Uiso 1 calc . .
C7 C 0.23729(8) -0.14791(19) -0.22328(7) 0.0202(2) Uani 1 d . .
H7 H 0.209 -0.1681 -0.2813 0.024 Uiso 1 calc . .
C8 C 0.19064(8) -0.08413(18) -0.18341(7) 0.0185(2) Uani 1 d . .
H8 H 0.1302 -0.0607 -0.2146 0.022 Uiso 1 calc . .
C9 C 0.09219(8) 0.06091(17) -0.09922(7) 0.0178(2) Uani 1 d . .
H9 H 0.0632 0.0416 -0.1573 0.021 Uiso 1 calc . .
C10 C 0.04621(8) 0.12982(18) -0.05979(8) 0.0203(2) Uani 1 d . .
H10 H -0.0139 0.1571 -0.0906 0.024 Uiso 1 calc . .
C11 C 0.08785(8) 0.15962(18) 0.02559(8) 0.0202(2) Uani 1 d . .
H11 H 0.0563 0.2074 0.0529 0.024 Uiso 1 calc . .
C12 C 0.17498(8) 0.11935(17) 0.06995(8) 0.0172(2) Uani 1 d . .
H12 H 0.2029 0.1405 0.1279 0.021 Uiso 1 calc . .
C13 C 0.36347(7) -0.06506(15) 0.03827(7) 0.01272(18) Uani 1 d . .
C14 C 0.32045(7) -0.09143(15) -0.05136(7) 0.01258(18) Uani 1 d . .
C15 C 0.23081(7) -0.05291(15) -0.09713(7) 0.01342(19) Uani 1 d . .
C16 C 0.18159(7) 0.01826(15) -0.05513(7) 0.01330(19) Uani 1 d . .
C17 C 0.22363(7) 0.04742(15) 0.03132(7) 0.01315(19) Uani 1 d . .
C18 C 0.31581(7) 0.00320(15) 0.07889(7) 0.01326(19) Uani 1 d . .
C19 C 0.27073(7) -0.49579(15) 0.02970(6) 0.01258(18) Uani 1 d . .
C20 C 0.31781(7) -0.55697(15) -0.01152(7) 0.01298(19) Uani 1 d . .
C21 C 0.27592(7) -0.58474(15) -0.09685(7) 0.01375(19) Uani 1 d . .
C22 C 0.18706(7) -0.54747(16) -0.14140(7) 0.0146(2) Uani 1 d . .
C23 C 0.14100(7) -0.47996(16) -0.10041(7) 0.01420(19) Uani 1 d . .
C24 C 0.18247(7) -0.45555(15) -0.01485(7) 0.01299(19) Uani 1 d . .
Cl19 Cl 0.32126(2) -0.47078(4) 0.13480(2) 0.01700(6) Uani 1 d . .
Cl20 Cl 0.42720(2) -0.59619(4) 0.04268(2) 0.01832(6) Uani 1 d . .
Cl21 Cl 0.33317(2) -0.66442(4) -0.14692(2) 0.01921(6) Uani 1 d . .
Cl22 Cl 0.13455(2) -0.58545(5) -0.24588(2) 0.02212(7) Uani 1 d . .
Cl23 Cl 0.03319(2) -0.42428(5) -0.15541(2) 0.02195(7) Uani 1 d . .
Cl24 Cl 0.12497(2) -0.37555(4) 0.03492(2) 0.01732(6) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   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
C1 C2 1.3773(17) . ?
C1 C18 1.4090(15) . ?
C1 H1 0.95 . ?
C2 C3 1.3947(18) . ?
C2 H2 0.95 . ?
C3 C4 1.3765(16) . ?
C3 H3 0.95 . ?
C4 C13 1.4116(15) . ?
C4 H4 0.95 . ?
C5 C6 1.3767(16) . ?
C5 C14 1.4113(15) . ?
C5 H5 0.95 . ?
C6 C7 1.3943(18) . ?
C6 H6 0.95 . ?
C7 C8 1.3784(17) . ?
C7 H7 0.95 . ?
C8 C15 1.4133(15) . ?
C8 H8 0.95 . ?
C9 C10 1.3760(17) . ?
C9 C16 1.4139(15) . ?
C9 H9 0.95 . ?
C10 C11 1.3975(18) . ?
C10 H10 0.95 . ?
C11 C12 1.3780(17) . ?
C11 H11 0.95 . ?
C12 C17 1.4103(15) . ?
C12 H12 0.95 . ?
C13 C18 1.4145(15) . ?
C13 C14 1.4617(15) . ?
C14 C15 1.4137(15) . ?
C15 C16 1.4631(15) . ?
C16 C17 1.4139(15) . ?
C17 C18 1.4616(15) . ?
C19 C24 1.3945(15) . ?
C19 C20 1.3975(14) . ?
C19 Cl19 1.7088(11) . ?
C20 C21 1.3945(15) . ?
C20 Cl20 1.7121(11) . ?
C21 C22 1.3985(15) . ?
C21 Cl21 1.7113(11) . ?
C22 C23 1.3954(15) . ?
C22 Cl22 1.7124(11) . ?
C23 C24 1.3947(15) . ?
C23 Cl23 1.7149(11) . ?
C24 Cl24 1.7114(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C18 121.71(11) . . ?
C2 C1 H1 119.1 . . ?
C18 C1 H1 119.1 . . ?
C1 C2 C3 119.68(11) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 120.05(11) . . ?
C4 C3 H3 120 . . ?
C2 C3 H3 120 . . ?
C3 C4 C13 121.31(11) . . ?
C3 C4 H4 119.3 . . ?
C13 C4 H4 119.3 . . ?
C6 C5 C14 121.54(11) . . ?
C6 C5 H5 119.2 . . ?
C14 C5 H5 119.2 . . ?
C5 C6 C7 119.90(11) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 119.89(11) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C15 121.39(11) . . ?
C7 C8 H8 119.3 . . ?
C15 C8 H8 119.3 . . ?
C10 C9 C16 121.41(11) . . ?
C10 C9 H9 119.3 . . ?
C16 C9 H9 119.3 . . ?
C9 C10 C11 120.03(11) . . ?
C9 C10 H10 120 . . ?
C11 C10 H10 120 . . ?
C12 C11 C10 119.67(11) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C17 121.57(11) . . ?
C11 C12 H12 119.2 . . ?
C17 C12 H12 119.2 . . ?
C4 C13 C18 118.78(10) . . ?
C4 C13 C14 121.28(10) . . ?
C18 C13 C14 119.94(10) . . ?
C5 C14 C15 118.62(10) . . ?
C5 C14 C13 121.37(10) . . ?
C15 C14 C13 120.01(10) . . ?
C8 C15 C14 118.65(10) . . ?
C8 C15 C16 121.34(10) . . ?
C14 C15 C16 120.01(10) . . ?
C17 C16 C9 118.57(10) . . ?
C17 C16 C15 119.95(10) . . ?
C9 C16 C15 121.47(10) . . ?
C12 C17 C16 118.74(10) . . ?
C12 C17 C18 121.28(10) . . ?
C16 C17 C18 119.98(10) . . ?
C1 C18 C13 118.48(10) . . ?
C1 C18 C17 121.46(10) . . ?
C13 C18 C17 120.06(10) . . ?
C24 C19 C20 120.04(10) . . ?
C24 C19 Cl19 119.95(8) . . ?
C20 C19 Cl19 120.01(8) . . ?
C21 C20 C19 120.08(10) . . ?
C21 C20 Cl20 119.95(8) . . ?
C19 C20 Cl20 119.97(8) . . ?
C20 C21 C22 119.89(10) . . ?
C20 C21 Cl21 120.02(9) . . ?
C22 C21 Cl21 120.09(8) . . ?
C23 C22 C21 119.82(10) . . ?
C23 C22 Cl22 119.93(9) . . ?
C21 C22 Cl22 120.25(8) . . ?
C24 C23 C22 120.30(10) . . ?
C24 C23 Cl23 119.70(8) . . ?
C22 C23 Cl23 120.00(8) . . ?
C19 C24 C23 119.80(10) . . ?
C19 C24 Cl24 120.31(8) . . ?
C23 C24 Cl24 119.89(8) . . ?


# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF

_chemical_name_systematic        'Hexachlorobenzene-triphenylente adduct'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method ethylether
