# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

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

data_PEA
_database_code_depnum_ccdc_archive 'CCDC 2075150'
loop_
_audit_author_name
_audit_author_address
'Haichao Liu'
;Jilin University
China
;
_audit_update_record             
;
2021-04-03 deposited with the CCDC.	2021-06-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        9-(phenylethynyl)anthracene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H14'
_chemical_formula_sum            'C22 H14'
_chemical_formula_weight         278.33

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.900(2)
_cell_length_b                   5.5710(7)
_cell_length_c                   16.420(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.441(4)
_cell_angle_gamma                90
_cell_volume                     1536.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1165
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.068
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'D8 VENTURE PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11878
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.896
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2705
_reflns_number_gt                1002
_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 D8 Venture'
_computing_cell_refinement       'Bruker D8 Venture'
_computing_data_reduction        'Bruker D8 Venture'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1248P)²+0.2865P] 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         2705
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1999
_refine_ls_R_factor_gt           0.0779
_refine_ls_wR_factor_ref         0.3051
_refine_ls_wR_factor_gt          0.1928
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_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
C1 C 0.3434(3) 0.3217(8) 0.1532(3) 0.0628(12) Uani 1 1 d . . . . .
C2 C 0.3454(3) 0.4963(10) 0.2164(3) 0.0772(15) Uani 1 1 d . . . . .
H2 H 0.3057 0.4975 0.2512 0.093 Uiso 1 1 calc R U . . .
C3 C 0.4049(4) 0.6617(10) 0.2265(3) 0.0909(17) Uani 1 1 d . . . . .
H3 H 0.4053 0.7757 0.2679 0.109 Uiso 1 1 calc R U . . .
C4 C 0.4652(4) 0.6613(11) 0.1752(4) 0.0953(19) Uani 1 1 d . . . . .
H4 H 0.5054 0.7755 0.1829 0.114 Uiso 1 1 calc R U . . .
C5 C 0.4663(3) 0.4982(11) 0.1145(3) 0.0864(17) Uani 1 1 d . . . . .
H5 H 0.5079 0.4987 0.0820 0.104 Uiso 1 1 calc R U . . .
C6 C 0.4040(3) 0.3247(9) 0.1000(3) 0.0695(13) Uani 1 1 d . . . . .
C7 C 0.4014(3) 0.1630(9) 0.0354(3) 0.0774(15) Uani 1 1 d . . . . .
H7 H 0.4418 0.1663 0.0013 0.093 Uiso 1 1 calc R U . . .
C8 C 0.3401(3) -0.0045(9) 0.0199(3) 0.0686(13) Uani 1 1 d . . . . .
C9 C 0.3361(3) -0.1678(11) -0.0467(3) 0.0880(17) Uani 1 1 d . . . . .
H9 H 0.3745 -0.1602 -0.0830 0.106 Uiso 1 1 calc R U . . .
C10 C 0.2779(4) -0.3339(11) -0.0586(4) 0.100(2) Uani 1 1 d . . . . .
H10 H 0.2763 -0.4395 -0.1026 0.120 Uiso 1 1 calc R U . . .
C11 C 0.2198(3) -0.3463(10) -0.0038(4) 0.0910(17) Uani 1 1 d . . . . .
H11 H 0.1800 -0.4621 -0.0117 0.109 Uiso 1 1 calc R U . . .
C12 C 0.2206(3) -0.1930(9) 0.0600(3) 0.0798(15) Uani 1 1 d . . . . .
H12 H 0.1812 -0.2049 0.0951 0.096 Uiso 1 1 calc R U . . .
C13 C 0.2801(3) -0.0150(8) 0.0746(3) 0.0630(12) Uani 1 1 d . . . . .
C14 C 0.2826(3) 0.1468(8) 0.1401(3) 0.0622(12) Uani 1 1 d . . . . .
C15 C 0.2233(3) 0.1410(9) 0.1959(3) 0.0703(14) Uani 1 1 d . . . . .
C16 C 0.1745(3) 0.1407(9) 0.2440(3) 0.0732(14) Uani 1 1 d . . . . .
C17 C 0.1175(3) 0.1520(9) 0.3022(3) 0.0652(13) Uani 1 1 d . . . . .
C18 C 0.0586(3) -0.0206(10) 0.3034(3) 0.0776(15) Uani 1 1 d . . . . .
H18 H 0.0562 -0.1478 0.2666 0.093 Uiso 1 1 calc R U . . .
C19 C 0.0038(3) -0.0043(10) 0.3591(3) 0.0807(15) Uani 1 1 d . . . . .
H19 H -0.0356 -0.1205 0.3596 0.097 Uiso 1 1 calc R U . . .
C20 C 0.0069(3) 0.1820(11) 0.4138(3) 0.0862(16) Uani 1 1 d . . . . .
H20 H -0.0307 0.1937 0.4508 0.103 Uiso 1 1 calc R U . . .
C21 C 0.0658(4) 0.3509(10) 0.4136(4) 0.0922(17) Uani 1 1 d . . . . .
H21 H 0.0686 0.4761 0.4513 0.111 Uiso 1 1 calc R U . . .
C22 C 0.1203(3) 0.3365(9) 0.3585(3) 0.0823(15) Uani 1 1 d . . . . .
H22 H 0.1598 0.4527 0.3589 0.099 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C14 1.415(6) . ?
C1 C6 1.419(6) . ?
C1 C2 1.420(6) . ?
C2 C3 1.360(7) . ?
C3 C4 1.393(7) . ?
C4 C5 1.350(7) . ?
C5 C6 1.430(7) . ?
C6 C7 1.388(7) . ?
C7 C8 1.396(6) . ?
C8 C9 1.419(6) . ?
C8 C13 1.430(6) . ?
C9 C10 1.348(7) . ?
C10 C11 1.406(7) . ?
C11 C12 1.352(7) . ?
C12 C13 1.413(6) . ?
C13 C14 1.400(6) . ?
C14 C15 1.431(6) . ?
C15 C16 1.205(6) . ?
C16 C17 1.432(7) . ?
C17 C22 1.379(6) . ?
C17 C18 1.386(6) . ?
C18 C19 1.375(6) . ?
C19 C20 1.369(7) . ?
C20 C21 1.370(7) . ?
C21 C22 1.364(7) . ?

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
C14 C1 C6 118.5(5) . . ?
C14 C1 C2 122.7(5) . . ?
C6 C1 C2 118.8(5) . . ?
C3 C2 C1 120.6(5) . . ?
C2 C3 C4 120.4(6) . . ?
C5 C4 C3 121.3(6) . . ?
C4 C5 C6 120.5(5) . . ?
C7 C6 C1 120.0(5) . . ?
C7 C6 C5 121.8(5) . . ?
C1 C6 C5 118.3(5) . . ?
C6 C7 C8 122.1(5) . . ?
C7 C8 C9 122.6(5) . . ?
C7 C8 C13 118.6(5) . . ?
C9 C8 C13 118.8(5) . . ?
C10 C9 C8 121.5(5) . . ?
C9 C10 C11 119.5(6) . . ?
C12 C11 C10 121.2(6) . . ?
C11 C12 C13 121.4(5) . . ?
C14 C13 C12 122.8(5) . . ?
C14 C13 C8 119.6(5) . . ?
C12 C13 C8 117.6(5) . . ?
C13 C14 C1 121.2(4) . . ?
C13 C14 C15 120.9(4) . . ?
C1 C14 C15 117.9(4) . . ?
C16 C15 C14 178.3(6) . . ?
C15 C16 C17 177.2(6) . . ?
C22 C17 C18 118.6(5) . . ?
C22 C17 C16 120.3(5) . . ?
C18 C17 C16 121.1(5) . . ?
C19 C18 C17 120.1(5) . . ?
C20 C19 C18 120.5(5) . . ?
C19 C20 C21 119.6(5) . . ?
C22 C21 C20 120.4(5) . . ?
C21 C22 C17 120.9(5) . . ?

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.049



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/methanol'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_PEA-TCNB
_database_code_depnum_ccdc_archive 'CCDC 2075151'
loop_
_audit_author_name
_audit_author_address
'Haichao Liu'
;Jilin University
China
;
_audit_update_record             
;
2021-04-03 deposited with the CCDC.	2021-06-14 downloaded from the CCDC.
;
_audit_creation_date             2019-08-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
9-(phenylethynyl)anthracene_1,2,4,5-tetracyanobenzene
_chemical_formula_moiety         'C22 H14, 1.5(C10 H2 N4)'
_chemical_formula_sum            'C37 H17 N6'
_chemical_formula_weight         545.56
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.7595(5)
_cell_length_b                   7.9919(3)
_cell_length_c                   36.1641(16)
_cell_angle_alpha                90
_cell_angle_beta                 91.4780(18)
_cell_angle_gamma                90
_cell_volume                     2819.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.18
_cell_measurement_theta_min      3.03
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1124
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            55890
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         3.033
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4295
_reflns_number_total             6962
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.157
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         6962
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1199
_refine_ls_R_factor_gt           0.0668
_refine_ls_restrained_S_all      1.066
_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)+(0.0415P)²+1.6928P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1608
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C15(H15), C19(H19), C20(H20),
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28), C30(H30), C35(H35),
  C39(H39)
;
_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 0.95034(19) 0.7002(2) 0.18013(5) 0.0365(4) Uani 1 1 d . . . . .
C2 C 1.08779(19) 0.6462(2) 0.17959(5) 0.0353(4) Uani 1 1 d . . . . .
C3 C 1.1377(2) 0.8000(2) 0.23718(5) 0.0414(5) Uani 1 1 d . . . . .
C4 C 1.18289(19) 0.6938(2) 0.20788(5) 0.0369(4) Uani 1 1 d . . . . .
C5 C 0.9076(2) 0.8072(3) 0.20949(6) 0.0428(5) Uani 1 1 d . . . . .
C6 C 1.0024(2) 0.8538(3) 0.23693(6) 0.0471(5) Uani 1 1 d . . . . .
H6 H 0.973542 0.925067 0.256251 0.056 Uiso 1 1 calc R . . . .
C7 C 1.3572(2) 0.3099(3) 0.09579(6) 0.0493(5) Uani 1 1 d . . . . .
H7 H 1.415554 0.338909 0.116220 0.059 Uiso 1 1 calc R . . . .
C8 C 1.2245(2) 0.3706(2) 0.09368(5) 0.0399(5) Uani 1 1 d . . . . .
C9 C 1.3216(2) 0.6409(3) 0.20864(6) 0.0464(5) Uani 1 1 d . . . . .
H9 H 1.353952 0.572263 0.189266 0.056 Uiso 1 1 calc R . . . .
C10 C 0.8521(2) 0.6535(3) 0.15242(6) 0.0477(5) Uani 1 1 d . . . . .
H10 H 0.877849 0.580446 0.133072 0.057 Uiso 1 1 calc R . . . .
C11 C 1.2339(2) 0.8465(3) 0.26560(6) 0.0538(6) Uani 1 1 d . . . . .
H11 H 1.205524 0.917625 0.285001 0.065 Uiso 1 1 calc R . . . .
C12 C 0.9010(2) 0.1110(3) 0.13209(6) 0.0422(5) Uani 1 1 d . . . . .
C13 C 1.1327(2) 0.5464(2) 0.14941(6) 0.0406(5) Uani 1 1 d . . . . .
C14 C 0.9205(2) 0.0033(3) 0.10207(6) 0.0432(5) Uani 1 1 d . . . . .
C15 C 1.0077(2) 0.1397(3) 0.15717(6) 0.0455(5) Uani 1 1 d . . . . .
H15 H 0.994403 0.210706 0.177836 0.055 Uiso 1 1 calc R . . . .
C16 C 1.1339(2) 0.0652(3) 0.15222(6) 0.0456(5) Uani 1 1 d . . . . .
C17 C 1.1530(2) -0.0432(3) 0.12235(6) 0.0453(5) Uani 1 1 d . . . . .
C19 C 1.4093(2) 0.6870(3) 0.23675(7) 0.0541(6) Uani 1 1 d . . . . .
H19 H 1.501391 0.648585 0.236981 0.065 Uiso 1 1 calc R . . . .
C20 C 1.0456(2) -0.0739(3) 0.09751(6) 0.0476(5) Uani 1 1 d . . . . .
H20 H 1.057986 -0.148078 0.077340 0.057 Uiso 1 1 calc R . . . .
C21 C 1.1728(2) 0.4697(3) 0.12336(6) 0.0432(5) Uani 1 1 d . . . . .
C22 C 1.1405(2) 0.3297(3) 0.06326(6) 0.0514(6) Uani 1 1 d . . . . .
H22 H 1.049767 0.372248 0.061272 0.062 Uiso 1 1 calc R . . . .
C23 C 0.7216(2) 0.7123(3) 0.15329(7) 0.0587(6) Uani 1 1 d . . . . .
H23 H 0.657175 0.679557 0.134522 0.070 Uiso 1 1 calc R . . . .
C24 C 1.3646(3) 0.7914(3) 0.26555(7) 0.0576(6) Uani 1 1 d . . . . .
H24 H 1.426810 0.822989 0.284954 0.069 Uiso 1 1 calc R . . . .
C25 C 0.7698(2) 0.8650(3) 0.20903(7) 0.0571(6) Uani 1 1 d . . . . .
H25 H 0.740088 0.935753 0.228358 0.069 Uiso 1 1 calc R . . . .
C26 C 1.4050(3) 0.2072(3) 0.06820(7) 0.0601(7) Uani 1 1 d . . . . .
H26 H 1.496000 0.165192 0.069835 0.072 Uiso 1 1 calc R . . . .
C27 C 1.2832(2) -0.1209(3) 0.11664(7) 0.0570(6) Uani 1 1 d . . . . .
C28 C 0.6802(2) 0.8212(3) 0.18160(7) 0.0621(7) Uani 1 1 d . . . . .
H28 H 0.589291 0.863732 0.181383 0.074 Uiso 1 1 calc R . . . .
C29 C 0.7714(2) 0.1933(3) 0.13600(6) 0.0541(6) Uani 1 1 d . . . . .
C30 C 1.1905(3) 0.2262(3) 0.03592(7) 0.0638(7) Uani 1 1 d . . . . .
H30 H 1.133331 0.197252 0.015244 0.077 Uiso 1 1 calc R . . . .
C34 C 0.8090(3) -0.0240(3) 0.07586(7) 0.0584(6) Uani 1 1 d . . . . .
C35 C 1.3217(3) 0.1655(3) 0.03851(7) 0.0652(7) Uani 1 1 d . . . . .
H35 H 1.355021 0.094497 0.019699 0.078 Uiso 1 1 calc R . . . .
C36 C 1.2460(3) 0.1034(3) 0.17738(7) 0.0612(7) Uani 1 1 d . . . . .
N4 N 1.3860(2) -0.1840(3) 0.11128(7) 0.0776(7) Uani 1 1 d . . . . .
N2 N 0.6695(2) 0.2611(3) 0.13821(7) 0.0816(7) Uani 1 1 d . . . . .
N1 N 0.7193(3) -0.0429(4) 0.05551(7) 0.0896(8) Uani 1 1 d . . . . .
N3 N 1.3341(3) 0.1376(4) 0.19705(8) 0.0958(9) Uani 1 1 d . . . . .
N6 N 1.1612(3) 0.7542(3) 0.01967(7) 0.0816(7) Uani 1 1 d . . . . .
C37 C 1.3871(2) 0.4865(3) -0.02347(6) 0.0512(6) Uani 1 1 d . . . . .
C40 C 1.2598(3) 0.6827(3) 0.01478(7) 0.0568(6) Uani 1 1 d . . . . .
C38 C 1.3831(2) 0.5905(3) 0.00763(6) 0.0481(5) Uani 1 1 d . . . . .
C39 C 1.4959(2) 0.6036(3) 0.03106(6) 0.0528(6) Uani 1 1 d . . . . .
H39 H 1.493434 0.673802 0.052230 0.063 Uiso 1 1 calc R . . . .
C41 C 1.2674(3) 0.4733(4) -0.04723(8) 0.0762(9) Uani 1 1 d . . . . .
N1B N 1.1705(3) 0.4644(5) -0.06504(8) 0.1290(14) 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
C1 C2 1.410(3) . ?
C1 C5 1.434(3) . ?
C1 C10 1.419(3) . ?
C2 C4 1.416(3) . ?
C2 C13 1.430(3) . ?
C3 C4 1.436(3) . ?
C3 C6 1.388(3) . ?
C3 C11 1.423(3) . ?
C4 C9 1.418(3) . ?
C5 C6 1.390(3) . ?
C5 C25 1.422(3) . ?
C7 C8 1.383(3) . ?
C7 C26 1.382(3) . ?
C8 C21 1.436(3) . ?
C8 C22 1.394(3) . ?
C9 C19 1.362(3) . ?
C10 C23 1.359(3) . ?
C11 C24 1.350(3) . ?
C12 C14 1.402(3) . ?
C12 C15 1.382(3) . ?
C12 C29 1.436(3) . ?
C13 C21 1.198(3) . ?
C14 C20 1.382(3) . ?
C14 C34 1.441(3) . ?
C15 C16 1.384(3) . ?
C16 C17 1.401(3) . ?
C16 C36 1.437(3) . ?
C17 C20 1.384(3) . ?
C17 C27 1.434(3) . ?
C19 C24 1.412(3) . ?
C22 C30 1.387(3) . ?
C23 C28 1.411(4) . ?
C25 C28 1.351(3) . ?
C26 C35 1.371(4) . ?
C27 N4 1.144(3) . ?
C29 N2 1.137(3) . ?
C30 C35 1.370(4) . ?
C34 N1 1.139(3) . ?
C36 N3 1.135(3) . ?
N6 C40 1.136(3) . ?
C37 C38 1.400(3) . ?
C37 C39 1.384(3) 3_865 ?
C37 C41 1.436(4) . ?
C40 C38 1.440(3) . ?
C38 C39 1.376(3) . ?
C41 N1B 1.133(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 C1 C5 119.23(18) . . ?
C2 C1 C10 122.37(18) . . ?
C10 C1 C5 118.40(18) . . ?
C1 C2 C4 120.94(17) . . ?
C1 C2 C13 119.48(18) . . ?
C4 C2 C13 119.56(17) . . ?
C6 C3 C4 119.23(19) . . ?
C6 C3 C11 122.3(2) . . ?
C11 C3 C4 118.51(19) . . ?
C2 C4 C3 118.94(17) . . ?
C2 C4 C9 122.81(19) . . ?
C9 C4 C3 118.25(19) . . ?
C6 C5 C1 119.14(18) . . ?
C6 C5 C25 122.3(2) . . ?
C25 C5 C1 118.6(2) . . ?
C3 C6 C5 122.52(19) . . ?
C26 C7 C8 120.1(2) . . ?
C7 C8 C21 119.9(2) . . ?
C7 C8 C22 119.5(2) . . ?
C22 C8 C21 120.57(19) . . ?
C19 C9 C4 121.0(2) . . ?
C23 C10 C1 120.6(2) . . ?
C24 C11 C3 121.3(2) . . ?
C14 C12 C29 119.67(19) . . ?
C15 C12 C14 119.65(19) . . ?
C15 C12 C29 120.7(2) . . ?
C21 C13 C2 176.8(2) . . ?
C12 C14 C34 119.14(19) . . ?
C20 C14 C12 120.30(19) . . ?
C20 C14 C34 120.6(2) . . ?
C12 C15 C16 120.1(2) . . ?
C15 C16 C17 120.15(19) . . ?
C15 C16 C36 119.5(2) . . ?
C17 C16 C36 120.3(2) . . ?
C16 C17 C27 121.0(2) . . ?
C20 C17 C16 119.8(2) . . ?
C20 C17 C27 119.2(2) . . ?
C9 C19 C24 120.7(2) . . ?
C14 C20 C17 120.0(2) . . ?
C13 C21 C8 176.5(2) . . ?
C30 C22 C8 119.5(2) . . ?
C10 C23 C28 121.1(2) . . ?
C11 C24 C19 120.2(2) . . ?
C28 C25 C5 121.2(2) . . ?
C35 C26 C7 120.3(2) . . ?
N4 C27 C17 178.4(3) . . ?
C25 C28 C23 120.0(2) . . ?
N2 C29 C12 178.0(3) . . ?
C35 C30 C22 120.5(2) . . ?
N1 C34 C14 178.5(3) . . ?
C30 C35 C26 120.1(2) . . ?
N3 C36 C16 178.3(3) . . ?
C38 C37 C41 119.0(2) . . ?
C39 C37 C38 120.6(2) 3_865 . ?
C39 C37 C41 120.4(2) 3_865 . ?
N6 C40 C38 178.4(3) . . ?
C37 C38 C40 119.3(2) . . ?
C39 C38 C37 120.1(2) . . ?
C39 C38 C40 120.6(2) . . ?
C38 C39 C37 119.3(2) . 3_865 ?
N1B C41 C37 177.8(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/acetonitrile'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_PEA-OFN
_database_code_depnum_ccdc_archive 'CCDC 2075152'
loop_
_audit_author_name
_audit_author_address
'Haichao Liu'
;Jilin University
China
;
_audit_update_record             
;
2021-04-03 deposited with the CCDC.	2021-06-14 downloaded from the CCDC.
;
_audit_creation_date             2019-08-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
9-(phenylethynyl)anthracene_octafluoronaphthalene
_chemical_formula_moiety         'C10 F8, C22 H14'
_chemical_formula_sum            'C32 H14 F8'
_chemical_formula_weight         550.43
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   6.8012(4)
_cell_length_b                   24.7708(15)
_cell_length_c                   14.5619(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.513(2)
_cell_angle_gamma                90
_cell_volume                     2403.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.72
_cell_measurement_theta_min      2.97
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needlelike
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            40935
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.789
_diffrn_reflns_theta_min         2.971
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2813
_reflns_number_total             5120
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.230
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1417
_refine_ls_R_factor_gt           0.0784
_refine_ls_restrained_S_all      1.074
_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)+(0.0366P)²+2.9066P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1464
_refine_ls_wR_factor_ref         0.1760
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C5AA(H5AA), C7AA(H7AA), C3AA(H3AA), C1AA(H1AA), C2AA(H2AA),
 C22(H22), C20(H20), C19(H19), C18(H18), C21(H21), C0AA(H0AA), C10(H10), C9(H9)
;
_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
C29 C 0.8943(5) 0.29419(13) 0.9845(2) 0.0472(8) Uani 1 1 d . . . . .
C25 C 0.8298(4) 0.37784(12) 0.8975(2) 0.0374(7) Uani 1 1 d . . . . .
C11 C 0.4260(5) 0.18508(14) 0.5622(2) 0.0476(8) Uani 1 1 d . . . . .
H11 H 0.434449 0.223345 0.561125 0.057 Uiso 1 1 calc R . . . .
C5AA C 0.3167(5) 0.06962(13) 0.3968(2) 0.0483(8) Uani 1 1 d . . . . .
H5AA H 0.307322 0.031415 0.399502 0.058 Uiso 1 1 calc R . . . .
C7AA C 0.4009(5) 0.07335(14) 0.5696(3) 0.0557(9) Uani 1 1 d . . . . .
H7AA H 0.390950 0.035188 0.573339 0.067 Uiso 1 1 calc R . . . .
C26 C 0.8669(5) 0.40473(13) 0.9841(2) 0.0456(8) Uani 1 1 d . . . . .
C27 C 0.9154(5) 0.37744(15) 1.0658(2) 0.0521(9) Uani 1 1 d . . . . .
C28 C 0.9299(5) 0.32204(16) 1.0657(2) 0.0537(9) Uani 1 1 d . . . . .
C30 C 0.8414(4) 0.32065(11) 0.8973(2) 0.0375(7) Uani 1 1 d . . . . .
C32 C 0.7520(5) 0.32113(15) 0.7290(2) 0.0513(8) Uani 1 1 d . . . . .
C24 C 0.7824(5) 0.40462(13) 0.8103(2) 0.0456(8) Uani 1 1 d . . . . .
C23 C 0.7456(5) 0.37697(15) 0.7290(2) 0.0506(8) Uani 1 1 d . . . . .
F8 F 0.7094(3) 0.29505(10) 0.64702(15) 0.0812(7) Uani 1 1 d . . . . .
F1 F 0.7024(3) 0.40299(10) 0.64645(14) 0.0803(7) Uani 1 1 d . . . . .
F6 F 0.9110(3) 0.24016(8) 0.98760(16) 0.0766(7) Uani 1 1 d . . . . .
F5 F 0.9826(3) 0.29624(10) 1.14776(15) 0.0841(7) Uani 1 1 d . . . . .
F4 F 0.9480(3) 0.40405(10) 1.14783(14) 0.0820(7) Uani 1 1 d . . . . .
F2 F 0.7735(3) 0.45891(8) 0.80682(15) 0.0714(6) Uani 1 1 d . . . . .
F7 F 0.8037(3) 0.23948(8) 0.80775(16) 0.0736(6) Uani 1 1 d . . . . .
F3 F 0.8548(3) 0.45850(8) 0.98733(15) 0.0721(6) Uani 1 1 d . . . . .
C3AA C 0.2376(6) 0.06476(17) 0.2244(3) 0.0683(11) Uani 1 1 d . . . . .
H3AA H 0.231602 0.026471 0.226534 0.082 Uiso 1 1 calc R . . . .
C1AA C 0.2108(6) 0.1466(2) 0.1361(3) 0.0738(12) Uani 1 1 d . . . . .
H1AA H 0.186384 0.163877 0.076651 0.089 Uiso 1 1 calc R . . . .
C2AA C 0.2042(6) 0.0901(2) 0.1407(3) 0.0807(13) Uani 1 1 d . . . . .
H2AA H 0.176042 0.069491 0.084503 0.097 Uiso 1 1 calc R . . . .
C31 C 0.7995(4) 0.29372(13) 0.8108(2) 0.0467(8) Uani 1 1 d . . . . .
C17 C 0.3655(7) 0.34580(14) 0.3893(2) 0.0647(11) Uani 1 1 d . . . . .
C22 C 0.5472(8) 0.37116(17) 0.4222(3) 0.0860(14) Uani 1 1 d . . . . .
H22 H 0.664160 0.350220 0.444079 0.103 Uiso 1 1 calc R . . . .
C20 C 0.3911(13) 0.4566(2) 0.3940(3) 0.122(3) Uani 1 1 d . . . . .
H20 H 0.399339 0.494888 0.396504 0.146 Uiso 1 1 calc R . . . .
C19 C 0.2110(11) 0.4326(2) 0.3610(3) 0.115(2) Uani 1 1 d . . . . .
H19 H 0.095275 0.453976 0.339120 0.138 Uiso 1 1 calc R . . . .
C18 C 0.1968(8) 0.37631(17) 0.3593(3) 0.0869(14) Uani 1 1 d . . . . .
H18 H 0.070972 0.359299 0.337539 0.104 Uiso 1 1 calc R . . . .
C21 C 0.5588(11) 0.4268(2) 0.4233(3) 0.113(2) Uani 1 1 d . . . . .
H21 H 0.684258 0.444096 0.444614 0.136 Uiso 1 1 calc R . . . .
C14 C 0.2903(4) 0.15222(13) 0.3048(2) 0.0418(7) Uani 1 1 d . . . . .
C12 C 0.3759(4) 0.15629(12) 0.4762(2) 0.0377(7) Uani 1 1 d . . . . .
C4AA C 0.2818(4) 0.09473(13) 0.3098(2) 0.0464(8) Uani 1 1 d . . . . .
C6AA C 0.3650(4) 0.09863(12) 0.4801(2) 0.0412(7) Uani 1 1 d . . . . .
C15 C 0.3456(5) 0.23992(13) 0.3857(2) 0.0485(8) Uani 1 1 d . . . . .
C13 C 0.3368(4) 0.18225(11) 0.3884(2) 0.0378(7) Uani 1 1 d . . . . .
C0AA C 0.2514(5) 0.17708(16) 0.2150(2) 0.0557(9) Uani 1 1 d . . . . .
H0AA H 0.253872 0.215316 0.210204 0.067 Uiso 1 1 calc R . . . .
C10 C 0.4620(5) 0.15890(16) 0.6456(2) 0.0590(9) Uani 1 1 d . . . . .
H10 H 0.496353 0.178966 0.702155 0.071 Uiso 1 1 calc R . . . .
C9 C 0.4488(5) 0.10235(17) 0.6492(3) 0.0633(10) Uani 1 1 d . . . . .
H9 H 0.473833 0.084471 0.708106 0.076 Uiso 1 1 calc R . . . .
C16 C 0.3538(6) 0.28762(14) 0.3869(2) 0.0579(9) 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
C29 C28 1.348(5) . ?
C29 C30 1.411(4) . ?
C29 F6 1.343(4) . ?
C25 C26 1.404(4) . ?
C25 C30 1.419(4) . ?
C25 C24 1.412(4) . ?
C11 C12 1.422(4) . ?
C11 C10 1.356(4) . ?
C5AA C4AA 1.388(4) . ?
C5AA C6AA 1.392(4) . ?
C7AA C6AA 1.422(4) . ?
C7AA C9 1.347(5) . ?
C26 C27 1.351(4) . ?
C26 F3 1.336(4) . ?
C27 C28 1.376(5) . ?
C27 F4 1.343(4) . ?
C28 F5 1.339(4) . ?
C30 C31 1.403(4) . ?
C32 C23 1.384(5) . ?
C32 F8 1.337(4) . ?
C32 C31 1.353(5) . ?
C24 C23 1.347(4) . ?
C24 F2 1.347(4) . ?
C23 F1 1.343(4) . ?
F7 C31 1.345(4) . ?
C3AA C2AA 1.349(6) . ?
C3AA C4AA 1.428(5) . ?
C1AA C2AA 1.404(6) . ?
C1AA C0AA 1.356(5) . ?
C17 C22 1.384(6) . ?
C17 C18 1.370(6) . ?
C17 C16 1.443(5) . ?
C22 C21 1.380(6) . ?
C20 C19 1.360(8) . ?
C20 C21 1.355(8) . ?
C19 C18 1.397(6) . ?
C14 C4AA 1.428(4) . ?
C14 C13 1.407(4) . ?
C14 C0AA 1.422(4) . ?
C12 C6AA 1.432(4) . ?
C12 C13 1.408(4) . ?
C15 C13 1.431(4) . ?
C15 C16 1.183(4) . ?
C10 C9 1.405(5) . ?

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
C28 C29 C30 121.4(3) . . ?
F6 C29 C28 118.8(3) . . ?
F6 C29 C30 119.8(3) . . ?
C26 C25 C30 118.4(3) . . ?
C26 C25 C24 123.6(3) . . ?
C24 C25 C30 118.1(3) . . ?
C10 C11 C12 121.2(3) . . ?
C4AA C5AA C6AA 122.1(3) . . ?
C9 C7AA C6AA 121.4(3) . . ?
C27 C26 C25 121.5(3) . . ?
F3 C26 C25 120.2(3) . . ?
F3 C26 C27 118.3(3) . . ?
C26 C27 C28 120.2(3) . . ?
F4 C27 C26 120.4(3) . . ?
F4 C27 C28 119.4(3) . . ?
C29 C28 C27 120.7(3) . . ?
F5 C28 C29 120.5(3) . . ?
F5 C28 C27 118.8(3) . . ?
C29 C30 C25 117.8(3) . . ?
C31 C30 C29 123.8(3) . . ?
C31 C30 C25 118.4(3) . . ?
F8 C32 C23 118.8(3) . . ?
F8 C32 C31 121.0(3) . . ?
C31 C32 C23 120.3(3) . . ?
C23 C24 C25 121.4(3) . . ?
F2 C24 C25 120.2(3) . . ?
F2 C24 C23 118.4(3) . . ?
C24 C23 C32 120.5(3) . . ?
F1 C23 C32 118.8(3) . . ?
F1 C23 C24 120.7(3) . . ?
C2AA C3AA C4AA 120.9(4) . . ?
C0AA C1AA C2AA 121.2(4) . . ?
C3AA C2AA C1AA 120.3(4) . . ?
C32 C31 C30 121.4(3) . . ?
F7 C31 C30 120.2(3) . . ?
F7 C31 C32 118.3(3) . . ?
C22 C17 C16 120.2(4) . . ?
C18 C17 C22 119.5(4) . . ?
C18 C17 C16 120.3(4) . . ?
C21 C22 C17 120.2(5) . . ?
C21 C20 C19 121.0(5) . . ?
C20 C19 C18 119.8(6) . . ?
C17 C18 C19 119.6(5) . . ?
C20 C21 C22 119.9(6) . . ?
C13 C14 C4AA 119.2(3) . . ?
C13 C14 C0AA 122.3(3) . . ?
C0AA C14 C4AA 118.5(3) . . ?
C11 C12 C6AA 118.0(3) . . ?
C13 C12 C11 122.6(3) . . ?
C13 C12 C6AA 119.3(3) . . ?
C5AA C4AA C3AA 122.0(3) . . ?
C5AA C4AA C14 119.4(3) . . ?
C14 C4AA C3AA 118.6(3) . . ?
C5AA C6AA C7AA 122.6(3) . . ?
C5AA C6AA C12 119.0(3) . . ?
C7AA C6AA C12 118.4(3) . . ?
C16 C15 C13 177.7(4) . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 C15 120.5(3) . . ?
C12 C13 C15 118.6(3) . . ?
C1AA C0AA C14 120.5(4) . . ?
C11 C10 C9 120.6(3) . . ?
C7AA C9 C10 120.4(3) . . ?
C15 C16 C17 179.3(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/methanol'
_exptl_crystal_preparation       Luminescent
