# 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_1-190k
_database_code_depnum_ccdc_archive 'CCDC 1954373'
loop_
_audit_author_name
_audit_author_address
'Binoy K. Saha'
;Pondicherry University
India
;
_audit_update_record             
;
2019-10-16 deposited with the CCDC.	2019-10-21 downloaded from the CCDC.
;
_audit_creation_date             2019-10-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            
;
Hexamethylbenzene . Tetrafluoro-1,4-benzoquinone
;
_chemical_name_systematic        
;
Hexamethylbenzene . Tetrafluoro-1,4-benzoquinone 
;
_chemical_formula_moiety         'C12 H18, C6 F4 O2'
_chemical_formula_sum            'C18 H18 F4 O2'
_chemical_formula_weight         342.32
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           166
_space_group_name_H-M_alt        'R -3 m'
_space_group_name_Hall           '-R 3 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, -y, -z'
'-x, -x+y, -z'
'y, x, -z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'-x+2/3, -x+y+1/3, -z+1/3'
'y+2/3, x+1/3, -z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x+1/3, -x+y+2/3, -z+2/3'
'y+1/3, x+2/3, -z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+y, y, z'
'x, x-y, z'
'-y, -x, z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+y+2/3, y+1/3, z+1/3'
'x+2/3, x-y+1/3, z+1/3'
'-y+2/3, -x+1/3, z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-x+y+1/3, y+2/3, z+2/3'
'x+1/3, x-y+2/3, z+2/3'
'-y+1/3, -x+2/3, z+2/3'

_cell_length_a                   14.5418(12)
_cell_length_b                   14.5418(12)
_cell_length_c                   6.6076(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1210.1(2)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    377
_cell_measurement_temperature    190(2)
_cell_measurement_theta_min      4.4622
_cell_measurement_theta_max      28.7398
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.909
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_min  0.19295
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rod shape'
_exptl_crystal_F_000             534
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            1388
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.803
_diffrn_reflns_theta_min         4.471
_diffrn_ambient_temperature      190(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                273
_reflns_number_total             364
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     33
_refine_ls_number_reflns         364
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0516P)²+0.4920P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1166
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H2A(0.5) H2B(0.5) H2C(0.5) O1(0.16666) F1A(0.33333)
3.a Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.000000 0.09631(10) 0.500000 0.0355(5) Uani 1 2 d S T P . .
C2 C 0.000000 0.20030(13) 0.500000 0.0618(7) Uani 1 2 d S T P . .
H2A H -0.039915 0.202811 0.617327 0.093 Uiso 0.5 1 calc GR . . . .
H2B H -0.033355 0.206091 0.375454 0.093 Uiso 0.5 1 calc GR . . . .
H2C H 0.073269 0.259403 0.507218 0.093 Uiso 0.5 1 calc GR . . . .
O1 O 0.5589(8) 0.1178(15) 0.3349(18) 0.063(4) Uani 0.3333 2 d S T P A 1
C3 C 0.61072(8) 0.22143(15) 0.3335(3) 0.0592(7) Uani 1 2 d S T P . .
F1A F 0.5683(15) 0.1210(7) 0.3335(11) 0.147(4) Uani 0.3333 1 d . . . A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C1 1.4005(14) 21_556 ?
C1 C1 1.4005(14) 20_556 ?
C1 C2 1.512(2) . ?
C2 H2A 0.9800 5_556 ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2B 0.9800 5_556 ?
C2 H2C 0.9800 . ?
C2 H2C 0.9800 5_556 ?
O1 C3 1.305(19) . ?
C3 C3 1.4092(19) 32 ?
C3 C3 1.4093(19) 33_545 ?
C3 F1A 1.270(10) 22_655 ?
C3 F1A 1.270(10) . ?
F1A F1A 0.23(5) 22_655 ?

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 C1 C1 120.0 21_556 20_556 ?
C1 C1 C2 120.0 21_556 . ?
C1 C1 C2 120.0 20_556 . ?
C1 C2 H2A 109.473(4) . 5_556 ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2B 109.473(3) . 5_556 ?
C1 C2 H2C 109.47(2) . 5_556 ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2A 141.1 . 5_556 ?
H2A C2 H2B 56.2 . 5_556 ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 5_556 5_556 ?
H2A C2 H2C 56.3 . 5_556 ?
H2A C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 5_556 5_556 ?
H2B C2 H2A 56.2 . 5_556 ?
H2B C2 H2B 141.1 . 5_556 ?
H2B C2 H2C 56.3 . 5_556 ?
H2B C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 5_556 5_556 ?
H2C C2 H2A 56.3 . 5_556 ?
H2C C2 H2B 56.3 . 5_556 ?
H2C C2 H2C 141.1 . 5_556 ?
O1 C3 C3 119.999(4) . 32 ?
O1 C3 C3 119.996(4) . 33_545 ?
C3 C3 C3 120.004(1) 32 33_545 ?
F1A C3 C3 125.1(10) . 32 ?
F1A C3 C3 114.9(10) 22_655 32 ?
F1A C3 F1A 10(2) . 22_655 ?
F1A F1A C3 84.9(10) 22_655 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C3 F1A F1A -0.1(3) 32 . . 22_655 ?
C3 C3 F1A F1A -179.9(3) 33_545 . . 22_655 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1-298k
_database_code_depnum_ccdc_archive 'CCDC 1954374'
loop_
_audit_author_name
_audit_author_address
'Binoy K. Saha'
;Pondicherry University
India
;
_audit_update_record             
;
2019-10-16 deposited with the CCDC.	2019-10-21 downloaded from the CCDC.
;
_audit_creation_date             2019-10-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            
;
Hexamethylbenzene . Tetrafluoro-1,4-benzoquinone
;
_chemical_name_systematic        
;
Hexamethylbenzene . Tetrafluoro-1,4-benzoquinone
;
_chemical_formula_moiety         'C12 H18, C6 F4 O2'
_chemical_formula_sum            'C18 H18 F4 O2'
_chemical_formula_weight         342.32
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           166
_space_group_name_H-M_alt        'R -3 m'
_space_group_name_Hall           '-R 3 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, -y, -z'
'-x, -x+y, -z'
'y, x, -z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'-x+2/3, -x+y+1/3, -z+1/3'
'y+2/3, x+1/3, -z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x+1/3, -x+y+2/3, -z+2/3'
'y+1/3, x+2/3, -z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+y, y, z'
'x, x-y, z'
'-y, -x, z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+y+2/3, y+1/3, z+1/3'
'x+2/3, x-y+1/3, z+1/3'
'-y+2/3, -x+1/3, z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-x+y+1/3, y+2/3, z+2/3'
'x+1/3, x-y+2/3, z+2/3'
'-y+1/3, -x+2/3, z+2/3'

_cell_length_a                   14.6259(12)
_cell_length_b                   14.6259(12)
_cell_length_c                   6.7359(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1247.9(2)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    335
_cell_measurement_temperature    298(2)
_cell_measurement_theta_min      4.4250
_cell_measurement_theta_max      28.9585
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.912
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_min  0.61535
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'Rod shape'
_exptl_crystal_F_000             534
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3935
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.263
_diffrn_reflns_theta_min         4.417
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                249
_reflns_number_total             399
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     33
_refine_ls_number_reflns         399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0733P)²+0.3100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1561
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H2A(0.5) H2B(0.5) H2C(0.5) O1(0.16666) F1A(0.33333)
3.a Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.000000 0.09534(11) 0.500000 0.0612(6) Uani 1 2 d S T P . .
C2 C 0.000000 0.19908(15) 0.500000 0.1089(10) Uani 1 2 d S T P . .
H2A H -0.031713 0.205100 0.620411 0.163 Uiso 0.5 1 calc GR . . . .
H2B H -0.039598 0.201157 0.388150 0.163 Uiso 0.5 1 calc GR . . . .
H2C H 0.071311 0.256612 0.491439 0.163 Uiso 0.5 1 calc GR . . . .
O1 O 0.5603(5) 0.1205(9) 0.331(3) 0.099(5) Uani 0.3333 2 d S T P A 1
C3 C 0.61200(9) 0.22400(19) 0.3334(3) 0.1140(11) Uani 1 2 d S T P . .
F1A F 0.6102(9) 0.1279(6) 0.3349(12) 0.168(8) Uani 0.3333 1 d . . . A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C1 1.3944(16) 21_556 ?
C1 C1 1.3944(16) 20_556 ?
C1 C2 1.517(3) . ?
C2 H2A 0.9600 5_556 ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2B 0.9600 5_556 ?
C2 H2C 0.9600 . ?
C2 H2C 0.9600 5_556 ?
O1 C3 1.311(12) . ?
C3 C3 1.385(2) 33_545 ?
C3 C3 1.385(2) 32 ?
C3 F1A 1.393(10) 22_655 ?
C3 F1A 1.393(10) . ?
F1A F1A 1.35(3) 22_655 ?
F1A F1A 1.43(2) 17_655 ?

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 C1 C1 120.0 21_556 20_556 ?
C1 C1 C2 120.0 21_556 . ?
C1 C1 C2 120.0 20_556 . ?
C1 C2 H2A 109.472(5) . 5_556 ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2B 109.474(8) . 5_556 ?
C1 C2 H2C 109.47(4) . 5_556 ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2A 141.1 . 5_556 ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2B 56.2 . 5_556 ?
H2A C2 H2B 109.5 5_556 5_556 ?
H2A C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 5_556 5_556 ?
H2A C2 H2C 56.3 . 5_556 ?
H2B C2 H2A 56.2 . 5_556 ?
H2B C2 H2B 141.1 . 5_556 ?
H2B C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 5_556 5_556 ?
H2B C2 H2C 56.3 . 5_556 ?
H2C C2 H2A 56.3 . 5_556 ?
H2C C2 H2B 56.3 . 5_556 ?
H2C C2 H2C 141.1 . 5_556 ?
O1 C3 C3 119.995(9) . 33_545 ?
O1 C3 C3 119.997(8) . 32 ?
O1 C3 F1A 29.1(5) . 22_655 ?
C3 C3 C3 120.003(1) 32 33_545 ?
C3 C3 F1A 91.0(5) 33_545 . ?
C3 C3 F1A 149.0(5) 32 . ?
C3 C3 F1A 149.0(5) 33_545 22_655 ?
C3 C3 F1A 91.0(5) 32 22_655 ?
C3 F1A F1A 89.0(5) . 17_655 ?
F1A F1A C3 61.0(5) 22_655 . ?
F1A F1A F1A 149.991(19) 22_655 17_655 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C3 F1A F1A 0.4(6) 32 . . 22_655 ?
C3 C3 F1A F1A 179.8(5) 32 . . 17_655 ?
C3 C3 F1A F1A -0.8(7) 33_545 . . 17_655 ?
C3 C3 F1A F1A 179.8(3) 33_545 . . 22_655 ?
F1A C3 F1A F1A 179.4(5) 22_655 . . 17_655 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3-118k
_database_code_depnum_ccdc_archive 'CCDC 1954375'
loop_
_audit_author_name
_audit_author_address
'Binoy K. Saha'
;Pondicherry University
India
;
_audit_update_record             
;
2019-09-18 deposited with the CCDC.	2019-10-21 downloaded from the CCDC.
;
_audit_creation_date             2014-03-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_chemical_name_common            'Pyrene . 1,3,5-trinitrobenzene'
_chemical_name_systematic        
;
Pyrene . 1,3,5-trinitrobenzene 
;
_chemical_formula_moiety         'C6 H3 N3 O6, C16 H10'
_chemical_formula_sum            'C22 H13 N3 O6'
_chemical_formula_weight         415.35
_chemical_melting_point          ?
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'
O O 0.0106 0.0060 '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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.6469(4)
_cell_length_b                   8.4809(6)
_cell_length_c                   16.2117(12)
_cell_angle_alpha                93.121(6)
_cell_angle_beta                 95.577(6)
_cell_angle_gamma                101.583(6)
_cell_volume                     888.46(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2537
_cell_measurement_temperature    118(2)
_cell_measurement_theta_min      3.6545
_cell_measurement_theta_max      29.0871
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.9828
_exptl_absorpt_correction_T_min  0.9337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Rod shape'
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9229
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.15
_diffrn_reflns_theta_min         3.66
_diffrn_ambient_temperature      118(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.834
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3105
_reflns_number_total             4009
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4009
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0534P)²+0.0906P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1159
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C22(H22), C18(H18), C10(H10), C5(H5), C6(H6), C13(H13), C12(H12),
 C8(H8), C9(H9), C3(H3), C2(H2), C1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.11220(16) -0.05898(13) 0.11996(7) 0.0296(3) Uani 1 1 d . . .
O4 O 0.35770(17) 0.69632(14) 0.34135(7) 0.0315(3) Uani 1 1 d . . .
O5 O 0.26622(17) 0.20977(14) 0.48831(7) 0.0300(3) Uani 1 1 d . . .
O3 O 0.32105(16) 0.67901(13) 0.20661(7) 0.0297(3) Uani 1 1 d . . .
O2 O 0.20012(16) 0.15762(14) 0.05532(6) 0.0294(3) Uani 1 1 d . . .
N1 N 0.16850(17) 0.08766(16) 0.11845(7) 0.0209(3) Uani 1 1 d . . .
N2 N 0.32242(17) 0.61889(15) 0.27372(8) 0.0213(3) Uani 1 1 d . . .
N3 N 0.21641(18) 0.12485(16) 0.42295(8) 0.0227(3) Uani 1 1 d . . .
O6 O 0.15808(19) -0.02223(14) 0.41780(7) 0.0355(3) Uani 1 1 d . . .
C19 C 0.27837(19) 0.44150(18) 0.27262(9) 0.0175(3) Uani 1 1 d . . .
C17 C 0.20239(19) 0.18639(18) 0.19798(9) 0.0180(3) Uani 1 1 d . . .
C20 C 0.27223(19) 0.37136(18) 0.34795(9) 0.0177(3) Uani 1 1 d . . .
H20 H 0.2979 0.4349 0.3994 0.021 Uiso 1 1 calc . . R
C22 C 0.19196(19) 0.10870(18) 0.27070(9) 0.0190(3) Uani 1 1 d . . .
H22 H 0.1620 -0.0057 0.2700 0.023 Uiso 1 1 calc . . R
C21 C 0.2269(2) 0.20448(18) 0.34445(9) 0.0186(3) Uani 1 1 d . . .
C18 C 0.24496(19) 0.35274(18) 0.19694(9) 0.0183(3) Uani 1 1 d . . .
H18 H 0.2509 0.4037 0.1462 0.022 Uiso 1 1 calc . . R
C16 C 0.74548(18) 0.31650(17) 0.27451(8) 0.0149(3) Uani 1 1 d . . .
C7 C 0.70870(19) 0.16028(17) 0.30508(9) 0.0177(3) Uani 1 1 d . . .
C4 C 0.6995(2) 0.19242(19) 0.13069(9) 0.0200(3) Uani 1 1 d . . .
C11 C 0.78906(19) 0.45574(18) 0.33097(9) 0.0178(3) Uani 1 1 d . . .
C15 C 0.74004(18) 0.33227(17) 0.18724(8) 0.0162(3) Uani 1 1 d . . .
C10 C 0.7952(2) 0.43641(19) 0.41630(9) 0.0226(3) Uani 1 1 d . . .
H10 H 0.8235 0.5289 0.4547 0.027 Uiso 1 1 calc . . R
C14 C 0.7784(2) 0.48867(19) 0.15668(9) 0.0207(3) Uani 1 1 d . . .
C5 C 0.6600(2) 0.03681(19) 0.16373(10) 0.0232(3) Uani 1 1 d . . .
H5 H 0.6303 -0.0576 0.1267 0.028 Uiso 1 1 calc . . R
C6 C 0.6641(2) 0.02187(18) 0.24616(10) 0.0217(3) Uani 1 1 d . . .
H6 H 0.6367 -0.0830 0.2658 0.026 Uiso 1 1 calc . . R
C13 C 0.8209(2) 0.62695(19) 0.21561(10) 0.0241(3) Uani 1 1 d . . .
H13 H 0.8460 0.7318 0.1959 0.029 Uiso 1 1 calc . . R
C12 C 0.8260(2) 0.61244(18) 0.29833(10) 0.0229(3) Uani 1 1 d . . .
H12 H 0.8544 0.7067 0.3355 0.027 Uiso 1 1 calc . . R
C8 C 0.7172(2) 0.1468(2) 0.39088(9) 0.0226(3) Uani 1 1 d . . .
H8 H 0.6931 0.0430 0.4119 0.027 Uiso 1 1 calc . . R
C9 C 0.7603(2) 0.2836(2) 0.44548(9) 0.0252(3) Uani 1 1 d . . .
H9 H 0.7660 0.2727 0.5036 0.030 Uiso 1 1 calc . . R
C3 C 0.7005(2) 0.2119(2) 0.04565(9) 0.0286(4) Uani 1 1 d . . .
H3 H 0.6755 0.1194 0.0074 0.034 Uiso 1 1 calc . . R
C2 C 0.7376(2) 0.3639(2) 0.01662(10) 0.0351(4) Uani 1 1 d . . .
H2 H 0.7371 0.3746 -0.0414 0.042 Uiso 1 1 calc . . R
C1 C 0.7755(2) 0.5014(2) 0.07088(10) 0.0315(4) Uani 1 1 d . . .
H1 H 0.7997 0.6050 0.0497 0.038 Uiso 1 1 calc . . R


_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
O1 N1 1.2270(16) . ?
O4 N2 1.2239(17) . ?
O5 N3 1.2263(17) . ?
O3 N2 1.2265(15) . ?
O2 N1 1.2254(15) . ?
N1 C17 1.4711(19) . ?
N2 C19 1.4726(19) . ?
N3 O6 1.2253(17) . ?
N3 C21 1.4740(18) . ?
C19 C20 1.3879(19) . ?
C19 C18 1.379(2) . ?
C17 C22 1.3823(19) . ?
C17 C18 1.383(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.383(2) . ?
C22 H22 0.9500 . ?
C22 C21 1.381(2) . ?
C18 H18 0.9500 . ?
C16 C7 1.4233(19) . ?
C16 C11 1.417(2) . ?
C16 C15 1.4260(19) . ?
C7 C6 1.436(2) . ?
C7 C8 1.398(2) . ?
C4 C15 1.423(2) . ?
C4 C5 1.436(2) . ?
C4 C3 1.398(2) . ?
C11 C10 1.3995(19) . ?
C11 C12 1.441(2) . ?
C15 C14 1.425(2) . ?
C10 H10 0.9500 . ?
C10 C9 1.387(2) . ?
C14 C13 1.435(2) . ?
C14 C1 1.400(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.347(2) . ?
C6 H6 0.9500 . ?
C13 H13 0.9500 . ?
C13 C12 1.351(2) . ?
C12 H12 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.384(2) . ?
C9 H9 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.381(2) . ?
C2 H2 0.9500 . ?
C2 C1 1.387(3) . ?
C1 H1 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 C17 117.82(12) . . ?
O2 N1 O1 124.53(13) . . ?
O2 N1 C17 117.64(13) . . ?
O4 N2 O3 124.43(13) . . ?
O4 N2 C19 117.95(12) . . ?
O3 N2 C19 117.62(13) . . ?
O5 N3 C21 118.03(13) . . ?
O6 N3 O5 124.83(13) . . ?
O6 N3 C21 117.14(13) . . ?
C20 C19 N2 118.39(13) . . ?
C18 C19 N2 118.60(12) . . ?
C18 C19 C20 123.01(14) . . ?
C22 C17 N1 118.47(13) . . ?
C22 C17 C18 122.79(14) . . ?
C18 C17 N1 118.74(13) . . ?
C19 C20 H20 121.6 . . ?
C21 C20 C19 116.78(14) . . ?
C21 C20 H20 121.6 . . ?
C17 C22 H22 121.4 . . ?
C21 C22 C17 117.19(14) . . ?
C21 C22 H22 121.4 . . ?
C20 C21 N3 118.62(13) . . ?
C22 C21 N3 118.35(13) . . ?
C22 C21 C20 123.03(13) . . ?
C19 C18 C17 117.19(13) . . ?
C19 C18 H18 121.4 . . ?
C17 C18 H18 121.4 . . ?
C7 C16 C15 119.85(13) . . ?
C11 C16 C7 119.87(13) . . ?
C11 C16 C15 120.28(13) . . ?
C16 C7 C6 118.41(13) . . ?
C8 C7 C16 119.16(13) . . ?
C8 C7 C6 122.42(13) . . ?
C15 C4 C5 118.34(13) . . ?
C3 C4 C15 118.88(14) . . ?
C3 C4 C5 122.78(14) . . ?
C16 C11 C12 118.71(13) . . ?
C10 C11 C16 118.97(13) . . ?
C10 C11 C12 122.32(14) . . ?
C4 C15 C16 120.23(13) . . ?
C4 C15 C14 119.92(13) . . ?
C14 C15 C16 119.84(13) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 C11 120.71(14) . . ?
C9 C10 H10 119.6 . . ?
C15 C14 C13 118.36(13) . . ?
C1 C14 C15 118.92(15) . . ?
C1 C14 C13 122.71(14) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.42(14) . . ?
C6 C5 H5 119.3 . . ?
C7 C6 H6 119.1 . . ?
C5 C6 C7 121.72(14) . . ?
C5 C6 H6 119.1 . . ?
C14 C13 H13 119.0 . . ?
C12 C13 C14 121.95(14) . . ?
C12 C13 H13 119.0 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.85(14) . . ?
C13 C12 H12 119.6 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.49(14) . . ?
C9 C8 H8 119.8 . . ?
C10 C9 H9 119.6 . . ?
C8 C9 C10 120.79(14) . . ?
C8 C9 H9 119.6 . . ?
C4 C3 H3 119.6 . . ?
C2 C3 C4 120.78(16) . . ?
C2 C3 H3 119.6 . . ?
C3 C2 H2 119.5 . . ?
C3 C2 C1 121.04(15) . . ?
C1 C2 H2 119.5 . . ?
C14 C1 H1 119.8 . . ?
C2 C1 C14 120.45(15) . . ?
C2 C1 H1 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C17 C22 7.14(18) . . . . ?
O1 N1 C17 C18 -173.39(11) . . . . ?
O4 N2 C19 C20 2.13(17) . . . . ?
O4 N2 C19 C18 -177.92(11) . . . . ?
O5 N3 C21 C20 -6.28(18) . . . . ?
O5 N3 C21 C22 173.35(12) . . . . ?
O3 N2 C19 C20 -177.81(12) . . . . ?
O3 N2 C19 C18 2.13(17) . . . . ?
O2 N1 C17 C22 -172.29(11) . . . . ?
O2 N1 C17 C18 7.19(17) . . . . ?
N1 C17 C22 C21 179.25(11) . . . . ?
N1 C17 C18 C19 -179.23(11) . . . . ?
N2 C19 C20 C21 178.90(11) . . . . ?
N2 C19 C18 C17 -179.51(11) . . . . ?
O6 N3 C21 C20 173.69(12) . . . . ?
O6 N3 C21 C22 -6.68(18) . . . . ?
C19 C20 C21 N3 -179.32(11) . . . . ?
C19 C20 C21 C22 1.06(19) . . . . ?
C17 C22 C21 N3 179.91(11) . . . . ?
C17 C22 C21 C20 -0.5(2) . . . . ?
C20 C19 C18 C17 0.43(19) . . . . ?
C22 C17 C18 C19 0.22(19) . . . . ?
C18 C19 C20 C21 -1.04(19) . . . . ?
C18 C17 C22 C21 -0.20(19) . . . . ?
C16 C7 C6 C5 1.17(19) . . . . ?
C16 C7 C8 C9 0.15(19) . . . . ?
C16 C11 C10 C9 0.33(19) . . . . ?
C16 C11 C12 C13 -0.46(19) . . . . ?
C16 C15 C14 C13 -0.32(18) . . . . ?
C16 C15 C14 C1 179.01(12) . . . . ?
C7 C16 C11 C10 0.04(18) . . . . ?
C7 C16 C11 C12 179.90(11) . . . . ?
C7 C16 C15 C4 -0.47(18) . . . . ?
C7 C16 C15 C14 -179.51(11) . . . . ?
C7 C8 C9 C10 0.2(2) . . . . ?
C4 C15 C14 C13 -179.36(11) . . . . ?
C4 C15 C14 C1 -0.03(19) . . . . ?
C4 C5 C6 C7 -0.2(2) . . . . ?
C4 C3 C2 C1 0.2(2) . . . . ?
C11 C16 C7 C6 179.71(11) . . . . ?
C11 C16 C7 C8 -0.28(18) . . . . ?
C11 C16 C15 C4 179.00(11) . . . . ?
C11 C16 C15 C14 -0.04(18) . . . . ?
C11 C10 C9 C8 -0.5(2) . . . . ?
C15 C16 C7 C6 -0.81(18) . . . . ?
C15 C16 C7 C8 179.20(11) . . . . ?
C15 C16 C11 C10 -179.43(11) . . . . ?
C15 C16 C11 C12 0.43(18) . . . . ?
C15 C4 C5 C6 -1.10(19) . . . . ?
C15 C4 C3 C2 -0.8(2) . . . . ?
C15 C14 C13 C12 0.3(2) . . . . ?
C15 C14 C1 C2 -0.5(2) . . . . ?
C10 C11 C12 C13 179.39(12) . . . . ?
C14 C13 C12 C11 0.1(2) . . . . ?
C5 C4 C15 C16 1.42(18) . . . . ?
C5 C4 C15 C14 -179.54(11) . . . . ?
C5 C4 C3 C2 179.44(13) . . . . ?
C6 C7 C8 C9 -179.84(12) . . . . ?
C13 C14 C1 C2 178.75(13) . . . . ?
C12 C11 C10 C9 -179.53(12) . . . . ?
C8 C7 C6 C5 -178.84(12) . . . . ?
C3 C4 C15 C16 -178.34(12) . . . . ?
C3 C4 C15 C14 0.70(18) . . . . ?
C3 C4 C5 C6 178.65(13) . . . . ?
C3 C2 C1 C14 0.5(2) . . . . ?
C1 C14 C13 C12 -179.01(13) . . . . ?
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3-298k
_database_code_depnum_ccdc_archive 'CCDC 1954376'
loop_
_audit_author_name
_audit_author_address
'Binoy K. Saha'
;Pondicherry University
India
;
_audit_update_record             
;
2019-09-18 deposited with the CCDC.	2019-10-21 downloaded from the CCDC.
;
_audit_creation_date             2014-03-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_chemical_name_common            'Pyrene . 1,3,5-trinitrobenzene'
_chemical_name_systematic        
;
Pyrene . 1,3,5-trinitrobenzene
;
_chemical_formula_moiety         'C6 H3 N3 O6, C16 H10'
_chemical_formula_sum            'C22 H13 N3 O6'
_chemical_formula_weight         415.35
_chemical_melting_point          ?
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'
O O 0.0106 0.0060 '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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.7752(5)
_cell_length_b                   8.5522(9)
_cell_length_c                   16.3550(15)
_cell_angle_alpha                93.041(8)
_cell_angle_beta                 95.628(7)
_cell_angle_gamma                101.281(7)
_cell_volume                     922.34(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1494
_cell_measurement_temperature    298(2)
_cell_measurement_theta_min      3.7869
_cell_measurement_theta_max      29.1340
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.9834
_exptl_absorpt_correction_T_min  0.9360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rod shape'
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9322
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.20
_diffrn_reflns_theta_min         3.79
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2209
_reflns_number_total             4259
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.0571
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0672P)²+0.0423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1656
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C22(H22), C18(H18), C10(H10), C5(H5), C6(H6), C13(H13), C12(H12),
 C8(H8), C9(H9), C3(H3), C2(H2), C1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.1241(3) -0.0495(2) 0.11799(12) 0.0915(6) Uani 1 1 d . . .
O4 O 0.3626(3) 0.6902(2) 0.34139(14) 0.0943(6) Uani 1 1 d . . .
O5 O 0.2600(3) 0.2050(3) 0.48307(12) 0.0908(6) Uani 1 1 d . . .
O3 O 0.3306(3) 0.6775(2) 0.20861(14) 0.0938(6) Uani 1 1 d . . .
O2 O 0.2056(3) 0.1658(3) 0.05572(12) 0.0904(6) Uani 1 1 d . . .
N1 N 0.1768(3) 0.0950(3) 0.11734(13) 0.0654(5) Uani 1 1 d . . .
N2 N 0.3291(3) 0.6163(2) 0.27420(17) 0.0676(6) Uani 1 1 d . . .
N3 N 0.2160(3) 0.1235(3) 0.41834(14) 0.0689(6) Uani 1 1 d . . .
O6 O 0.1605(3) -0.0211(3) 0.41199(13) 0.1052(7) Uani 1 1 d . . .
C19 C 0.2828(3) 0.4405(2) 0.27204(14) 0.0504(5) Uani 1 1 d . . .
C17 C 0.2090(3) 0.1913(3) 0.19677(13) 0.0504(5) Uani 1 1 d . . .
C20 C 0.2736(3) 0.3689(3) 0.34538(14) 0.0523(5) Uani 1 1 d . . .
H20 H 0.2967 0.4291 0.3957 0.063 Uiso 1 1 calc . . R
C22 C 0.1962(3) 0.1130(3) 0.26784(14) 0.0515(5) Uani 1 1 d . . .
H22 H 0.1664 0.0019 0.2663 0.062 Uiso 1 1 calc . . R
C21 C 0.2287(3) 0.2044(3) 0.34113(13) 0.0509(5) Uani 1 1 d . . .
C18 C 0.2516(3) 0.3553(3) 0.19718(14) 0.0524(5) Uani 1 1 d . . .
H18 H 0.2588 0.4063 0.1484 0.063 Uiso 1 1 calc . . R
C16 C 0.7497(2) 0.3171(2) 0.27497(12) 0.0425(5) Uani 1 1 d . . .
C7 C 0.7111(3) 0.1633(3) 0.30478(16) 0.0579(6) Uani 1 1 d . . .
C4 C 0.7054(3) 0.1963(3) 0.13321(15) 0.0670(7) Uani 1 1 d . . .
C11 C 0.7925(3) 0.4541(3) 0.33199(15) 0.0563(6) Uani 1 1 d . . .
C15 C 0.7464(3) 0.3356(3) 0.18968(13) 0.0478(5) Uani 1 1 d . . .
C10 C 0.7954(4) 0.4332(4) 0.41535(18) 0.0827(8) Uani 1 1 d . . .
H10 H 0.8223 0.5220 0.4531 0.099 Uiso 1 1 calc . . R
C14 C 0.7851(3) 0.4898(3) 0.16042(17) 0.0691(7) Uani 1 1 d . . .
C5 C 0.6656(3) 0.0434(3) 0.1665(2) 0.0788(8) Uani 1 1 d . . .
H5 H 0.6366 -0.0484 0.1308 0.095 Uiso 1 1 calc . . R
C6 C 0.6688(3) 0.0291(3) 0.2473(2) 0.0778(8) Uani 1 1 d . . .
H6 H 0.6424 -0.0726 0.2664 0.093 Uiso 1 1 calc . . R
C13 C 0.8280(4) 0.6239(3) 0.2197(2) 0.0842(9) Uani 1 1 d . . .
H13 H 0.8549 0.7262 0.2014 0.101 Uiso 1 1 calc . . R
C12 C 0.8309(3) 0.6077(3) 0.3006(2) 0.0762(8) Uani 1 1 d . . .
H12 H 0.8585 0.6985 0.3371 0.091 Uiso 1 1 calc . . R
C8 C 0.7176(3) 0.1496(4) 0.3903(2) 0.0817(9) Uani 1 1 d . . .
H8 H 0.6935 0.0492 0.4109 0.098 Uiso 1 1 calc . . R
C9 C 0.7592(4) 0.2835(5) 0.4426(2) 0.0953(10) Uani 1 1 d . . .
H9 H 0.7631 0.2727 0.4990 0.114 Uiso 1 1 calc . . R
C3 C 0.7064(4) 0.2180(6) 0.0504(2) 0.1086(12) Uani 1 1 d . . .
H3 H 0.6814 0.1292 0.0127 0.130 Uiso 1 1 calc . . R
C2 C 0.7434(6) 0.3680(8) 0.0228(2) 0.1320(17) Uani 1 1 d . . .
H2 H 0.7413 0.3785 -0.0336 0.158 Uiso 1 1 calc . . R
C1 C 0.7835(5) 0.5035(6) 0.0754(3) 0.1120(13) Uani 1 1 d . . .
H1 H 0.8095 0.6039 0.0547 0.134 Uiso 1 1 calc . . R


_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
O1 N1 1.218(3) . ?
O4 N2 1.216(3) . ?
O5 N3 1.214(3) . ?
O3 N2 1.218(3) . ?
O2 N1 1.216(2) . ?
N1 C17 1.474(3) . ?
N2 C19 1.473(3) . ?
N3 O6 1.216(3) . ?
N3 C21 1.473(3) . ?
C19 C20 1.377(3) . ?
C19 C18 1.367(3) . ?
C17 C22 1.373(3) . ?
C17 C18 1.375(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.377(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.370(3) . ?
C18 H18 0.9300 . ?
C16 C7 1.412(3) . ?
C16 C11 1.423(3) . ?
C16 C15 1.411(3) . ?
C7 C6 1.409(4) . ?
C7 C8 1.407(4) . ?
C4 C15 1.433(3) . ?
C4 C5 1.431(4) . ?
C4 C3 1.377(4) . ?
C11 C10 1.383(4) . ?
C11 C12 1.422(3) . ?
C15 C14 1.411(3) . ?
C10 H10 0.9300 . ?
C10 C9 1.362(4) . ?
C14 C13 1.427(4) . ?
C14 C1 1.401(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.332(4) . ?
C6 H6 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.337(4) . ?
C12 H12 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.358(4) . ?
C9 H9 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.368(5) . ?
C2 H2 0.9300 . ?
C2 C1 1.372(5) . ?
C1 H1 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 C17 117.9(2) . . ?
O2 N1 O1 124.6(2) . . ?
O2 N1 C17 117.5(2) . . ?
O4 N2 O3 124.6(2) . . ?
O4 N2 C19 117.6(2) . . ?
O3 N2 C19 117.7(2) . . ?
O5 N3 O6 124.9(2) . . ?
O5 N3 C21 118.2(2) . . ?
O6 N3 C21 116.8(2) . . ?
C20 C19 N2 118.7(2) . . ?
C18 C19 N2 118.5(2) . . ?
C18 C19 C20 122.8(2) . . ?
C22 C17 N1 118.4(2) . . ?
C22 C17 C18 122.5(2) . . ?
C18 C17 N1 119.1(2) . . ?
C19 C20 H20 121.4 . . ?
C19 C20 C21 117.2(2) . . ?
C21 C20 H20 121.4 . . ?
C17 C22 H22 121.2 . . ?
C21 C22 C17 117.6(2) . . ?
C21 C22 H22 121.2 . . ?
C20 C21 N3 118.7(2) . . ?
C22 C21 N3 118.8(2) . . ?
C22 C21 C20 122.5(2) . . ?
C19 C18 C17 117.4(2) . . ?
C19 C18 H18 121.3 . . ?
C17 C18 H18 121.3 . . ?
C7 C16 C11 119.3(2) . . ?
C15 C16 C7 120.69(19) . . ?
C15 C16 C11 120.03(19) . . ?
C6 C7 C16 118.4(2) . . ?
C8 C7 C16 119.0(2) . . ?
C8 C7 C6 122.5(3) . . ?
C5 C4 C15 117.8(2) . . ?
C3 C4 C15 118.0(3) . . ?
C3 C4 C5 124.1(3) . . ?
C10 C11 C16 119.1(2) . . ?
C10 C11 C12 122.6(3) . . ?
C12 C11 C16 118.3(2) . . ?
C16 C15 C4 119.3(2) . . ?
C16 C15 C14 120.3(2) . . ?
C14 C15 C4 120.4(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 C11 120.5(3) . . ?
C9 C10 H10 119.7 . . ?
C15 C14 C13 117.8(2) . . ?
C1 C14 C15 118.7(3) . . ?
C1 C14 C13 123.4(3) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.7(2) . . ?
C6 C5 H5 119.1 . . ?
C7 C6 H6 119.0 . . ?
C5 C6 C7 122.0(2) . . ?
C5 C6 H6 119.0 . . ?
C14 C13 H13 118.8 . . ?
C12 C13 C14 122.3(2) . . ?
C12 C13 H13 118.8 . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.1(2) . . ?
C13 C12 H12 119.4 . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C10 C9 H9 118.9 . . ?
C8 C9 C10 122.3(3) . . ?
C8 C9 H9 118.9 . . ?
C4 C3 H3 119.5 . . ?
C2 C3 C4 121.0(4) . . ?
C2 C3 H3 119.5 . . ?
C3 C2 H2 118.9 . . ?
C3 C2 C1 122.3(4) . . ?
C1 C2 H2 118.9 . . ?
C14 C1 H1 120.2 . . ?
C2 C1 C14 119.5(4) . . ?
C2 C1 H1 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C17 C22 5.8(3) . . . . ?
O1 N1 C17 C18 -174.46(18) . . . . ?
O4 N2 C19 C20 2.0(3) . . . . ?
O4 N2 C19 C18 -177.78(19) . . . . ?
O5 N3 C21 C20 -5.3(3) . . . . ?
O5 N3 C21 C22 174.55(19) . . . . ?
O3 N2 C19 C20 -177.85(17) . . . . ?
O3 N2 C19 C18 2.4(3) . . . . ?
O2 N1 C17 C22 -173.91(17) . . . . ?
O2 N1 C17 C18 5.8(3) . . . . ?
N1 C17 C22 C21 179.31(16) . . . . ?
N1 C17 C18 C19 -179.27(16) . . . . ?
N2 C19 C20 C21 179.60(16) . . . . ?
N2 C19 C18 C17 179.87(15) . . . . ?
O6 N3 C21 C20 174.35(19) . . . . ?
O6 N3 C21 C22 -5.8(3) . . . . ?
C19 C20 C21 N3 -179.53(16) . . . . ?
C19 C20 C21 C22 0.7(3) . . . . ?
C17 C22 C21 N3 -179.97(15) . . . . ?
C17 C22 C21 C20 -0.2(3) . . . . ?
C20 C19 C18 C17 0.1(3) . . . . ?
C22 C17 C18 C19 0.4(3) . . . . ?
C18 C19 C20 C21 -0.6(3) . . . . ?
C18 C17 C22 C21 -0.4(3) . . . . ?
C16 C7 C6 C5 0.4(3) . . . . ?
C16 C7 C8 C9 0.5(3) . . . . ?
C16 C11 C10 C9 0.5(3) . . . . ?
C16 C11 C12 C13 -0.3(3) . . . . ?
C16 C15 C14 C13 0.3(3) . . . . ?
C16 C15 C14 C1 179.07(19) . . . . ?
C7 C16 C11 C10 0.0(3) . . . . ?
C7 C16 C11 C12 -179.98(16) . . . . ?
C7 C16 C15 C4 -0.6(2) . . . . ?
C7 C16 C15 C14 179.97(16) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
C4 C15 C14 C13 -179.06(18) . . . . ?
C4 C15 C14 C1 -0.3(3) . . . . ?
C4 C5 C6 C7 0.2(4) . . . . ?
C4 C3 C2 C1 0.8(5) . . . . ?
C11 C16 C7 C6 179.97(18) . . . . ?
C11 C16 C7 C8 -0.5(3) . . . . ?
C11 C16 C15 C4 179.26(16) . . . . ?
C11 C16 C15 C14 -0.1(2) . . . . ?
C11 C10 C9 C8 -0.5(4) . . . . ?
C15 C16 C7 C6 -0.1(3) . . . . ?
C15 C16 C7 C8 179.41(17) . . . . ?
C15 C16 C11 C10 -179.86(17) . . . . ?
C15 C16 C11 C12 0.1(3) . . . . ?
C15 C4 C5 C6 -0.9(3) . . . . ?
C15 C4 C3 C2 -0.6(4) . . . . ?
C15 C14 C13 C12 -0.5(3) . . . . ?
C15 C14 C1 C2 0.4(4) . . . . ?
C10 C11 C12 C13 179.7(2) . . . . ?
C14 C13 C12 C11 0.5(4) . . . . ?
C5 C4 C15 C16 1.2(3) . . . . ?
C5 C4 C15 C14 -179.45(18) . . . . ?
C5 C4 C3 C2 179.2(3) . . . . ?
C6 C7 C8 C9 180.0(2) . . . . ?
C13 C14 C1 C2 179.1(3) . . . . ?
C12 C11 C10 C9 -179.5(2) . . . . ?
C8 C7 C6 C5 -179.1(2) . . . . ?
C3 C4 C15 C16 -178.98(18) . . . . ?
C3 C4 C15 C14 0.4(3) . . . . ?
C3 C4 C5 C6 179.2(2) . . . . ?
C3 C2 C1 C14 -0.7(5) . . . . ?
C1 C14 C13 C12 -179.2(2) . . . . ?


