# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1880026'
_audit_update_record             
;
2018-12-04 deposited with the CCDC.
2019-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'Benzo[c]cinnoline + 1,4-Tetrafluorobenzene'
_chemical_name_common            ?
_chemical_melting_point          412
_chemical_formula_moiety         'C18 H8 F4 I2 N2'
_chemical_formula_sum            'C18 H8 F4 I2 N2'
_chemical_formula_weight         582.06

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   4.4893(2)
_cell_length_b                   15.5665(5)
_cell_length_c                   24.4653(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.894(2)
_cell_angle_gamma                90
_cell_volume                     1707.52(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9949
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      30.13

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.264
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    3.729
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_max  0.0824
_exptl_absorpt_correction_T_min  0.0082
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19414
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.551
_diffrn_reflns_theta_max         30.185
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5038
_reflns_number_gt                4509
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0543P)²+2.7060P] 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         5038
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1107
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.003
_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
I2 I 0.72111(7) 0.79731(2) 0.54697(2) 0.02842(10) Uani 1 1 d . . . . .
I1 I 0.12588(6) 0.60301(2) 0.60423(2) 0.01741(9) Uani 1 1 d . . . . .
F2 F 0.1658(6) 0.64076(16) 0.47429(10) 0.0254(6) Uani 1 1 d . . . . .
F1 F 0.5317(6) 0.43484(16) 0.60287(10) 0.0232(5) Uani 1 1 d . . . . .
F3 F 0.8904(6) 0.90741(17) 0.44396(12) 0.0291(6) Uani 1 1 d . . . . .
F4 F 0.7150(6) 1.05875(19) 0.40578(11) 0.0302(6) Uani 1 1 d . . . . .
N2 N 0.6792(7) 0.6352(2) 0.71603(14) 0.0177(7) Uani 1 1 d . . . . .
N1 N 0.8635(8) 0.6870(2) 0.69466(14) 0.0187(7) Uani 1 1 d . . . . .
C14 C 0.3414(9) 0.5408(3) 0.54130(16) 0.0181(8) Uani 1 1 d . . . . .
C13 C 0.5105(9) 0.4684(3) 0.55202(16) 0.0170(7) Uani 1 1 d . . . . .
C16 C 0.5890(9) 0.9182(3) 0.51974(18) 0.0202(8) Uani 1 1 d . . . . .
C15 C 0.3323(9) 0.5717(2) 0.48851(17) 0.0184(8) Uani 1 1 d . . . . .
C18 C 0.6050(9) 1.0317(3) 0.45284(17) 0.0199(8) Uani 1 1 d . . . . .
C17 C 0.6960(9) 0.9523(3) 0.47182(17) 0.0187(8) Uani 1 1 d . . . . .
C10 C 0.2598(10) 0.6037(3) 0.83755(19) 0.0223(9) Uani 1 1 d . . . . .
H10 H 0.126240 0.564105 0.850807 0.027 Uiso 1 1 calc R U . . .
C9 C 0.3496(10) 0.6750(3) 0.86961(19) 0.0231(9) Uani 1 1 d . . . . .
H9 H 0.275523 0.682060 0.904143 0.028 Uiso 1 1 calc R U . . .
C8 C 0.5468(9) 0.7348(3) 0.85037(17) 0.0191(8) Uani 1 1 d . . . . .
H8 H 0.604662 0.781585 0.872025 0.023 Uiso 1 1 calc R U . . .
C7 C 0.6601(8) 0.7250(3) 0.79823(17) 0.0169(7) Uani 1 1 d . . . . .
C6 C 0.8584(8) 0.7835(2) 0.77359(16) 0.0155(7) Uani 1 1 d . . . . .
C5 C 0.9659(9) 0.8610(3) 0.79711(17) 0.0194(8) Uani 1 1 d . . . . .
H5 H 0.907460 0.876666 0.831662 0.023 Uiso 1 1 calc R U . . .
C4 C 1.1528(9) 0.9134(3) 0.77043(18) 0.0201(8) Uani 1 1 d . . . . .
H4 H 1.219671 0.964331 0.786638 0.024 Uiso 1 1 calc R U . . .
C3 C 1.2452(10) 0.8903(3) 0.71814(18) 0.0210(8) Uani 1 1 d . . . . .
H3 H 1.372813 0.926181 0.699885 0.025 Uiso 1 1 calc R U . . .
C11 C 0.3686(9) 0.5928(3) 0.78705(19) 0.0201(8) Uani 1 1 d . . . . .
H11 H 0.308834 0.545779 0.765762 0.024 Uiso 1 1 calc R U . . .
C12 C 0.5725(8) 0.6529(3) 0.76697(17) 0.0166(7) Uani 1 1 d . . . . .
C1 C 0.9543(8) 0.7620(2) 0.72122(16) 0.0164(7) Uani 1 1 d . . . . .
C2 C 1.1482(9) 0.8159(3) 0.69446(16) 0.0186(8) Uani 1 1 d . . . . .
H2 H 1.211437 0.800759 0.660155 0.022 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
I2 C16 2.073(4) . ?
I1 C14 2.096(4) . ?
F2 C15 1.345(4) . ?
F1 C13 1.348(4) . ?
F3 C17 1.332(5) . ?
F4 C18 1.343(5) . ?
N2 N1 1.285(5) . ?
N2 C12 1.385(5) . ?
N1 C1 1.388(5) . ?
C14 C13 1.377(6) . ?
C14 C15 1.377(6) . ?
C13 C15 1.393(6) 3_666 ?
C16 C18 1.369(6) 3_676 ?
C16 C17 1.394(6) . ?
C18 C17 1.376(6) . ?
C10 C11 1.362(7) . ?
C10 C9 1.406(6) . ?
C10 H10 0.9300 . ?
C9 C8 1.383(6) . ?
C9 H9 0.9300 . ?
C8 C7 1.405(6) . ?
C8 H8 0.9300 . ?
C7 C12 1.403(5) . ?
C7 C6 1.428(6) . ?
C6 C5 1.412(5) . ?
C6 C1 1.412(6) . ?
C5 C4 1.360(6) . ?
C5 H5 0.9300 . ?
C4 C3 1.411(6) . ?
C4 H4 0.9300 . ?
C3 C2 1.357(6) . ?
C3 H3 0.9300 . ?
C11 C12 1.414(6) . ?
C11 H11 0.9300 . ?
C1 C2 1.396(6) . ?
C2 H2 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
N1 N2 C12 120.0(3) . . ?
N2 N1 C1 121.2(4) . . ?
C13 C14 C15 117.0(4) . . ?
C13 C14 I1 120.6(3) . . ?
C15 C14 I1 122.3(3) . . ?
F1 C13 C14 120.3(4) . . ?
F1 C13 C15 118.0(3) . 3_666 ?
C14 C13 C15 121.7(4) . 3_666 ?
C18 C16 C17 116.8(4) 3_676 . ?
C18 C16 I2 122.6(3) 3_676 . ?
C17 C16 I2 120.7(3) . . ?
F2 C15 C14 120.8(4) . . ?
F2 C15 C13 117.9(3) . 3_666 ?
C14 C15 C13 121.3(4) . 3_666 ?
F4 C18 C16 120.8(4) . 3_676 ?
F4 C18 C17 117.0(4) . . ?
C16 C18 C17 122.1(4) 3_676 . ?
F3 C17 C18 119.3(4) . . ?
F3 C17 C16 119.6(4) . . ?
C18 C17 C16 121.1(4) . . ?
C11 C10 C9 119.9(4) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C8 C9 C10 120.8(4) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C8 C7 120.2(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C12 C7 C8 118.5(4) . . ?
C12 C7 C6 116.3(4) . . ?
C8 C7 C6 125.2(4) . . ?
C5 C6 C1 117.3(4) . . ?
C5 C6 C7 125.5(4) . . ?
C1 C6 C7 117.2(3) . . ?
C4 C5 C6 121.5(4) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C2 C3 C4 120.1(4) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C10 C11 C12 120.0(4) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
N2 C12 C7 123.3(4) . . ?
N2 C12 C11 116.1(4) . . ?
C7 C12 C11 120.5(4) . . ?
N1 C1 C2 117.5(4) . . ?
N1 C1 C6 121.9(4) . . ?
C2 C1 C6 120.6(4) . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 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
C12 N2 N1 C1 -1.4(5) . . . . ?
C15 C14 C13 F1 179.5(3) . . . . ?
I1 C14 C13 F1 2.2(5) . . . . ?
C15 C14 C13 C15 0.5(7) . . . 3_666 ?
I1 C14 C13 C15 -176.8(3) . . . 3_666 ?
C13 C14 C15 F2 178.2(4) . . . . ?
I1 C14 C15 F2 -4.6(5) . . . . ?
C13 C14 C15 C13 -0.5(7) . . . 3_666 ?
I1 C14 C15 C13 176.8(3) . . . 3_666 ?
F4 C18 C17 F3 1.5(6) . . . . ?
C16 C18 C17 F3 -178.5(4) 3_676 . . . ?
F4 C18 C17 C16 -178.7(3) . . . . ?
C16 C18 C17 C16 1.3(7) 3_676 . . . ?
C18 C16 C17 F3 178.6(4) 3_676 . . . ?
I2 C16 C17 F3 -1.6(5) . . . . ?
C18 C16 C17 C18 -1.2(6) 3_676 . . . ?
I2 C16 C17 C18 178.7(3) . . . . ?
C11 C10 C9 C8 0.3(6) . . . . ?
C10 C9 C8 C7 0.1(6) . . . . ?
C9 C8 C7 C12 -1.1(6) . . . . ?
C9 C8 C7 C6 178.4(4) . . . . ?
C12 C7 C6 C5 177.9(4) . . . . ?
C8 C7 C6 C5 -1.6(6) . . . . ?
C12 C7 C6 C1 -1.9(5) . . . . ?
C8 C7 C6 C1 178.6(4) . . . . ?
C1 C6 C5 C4 0.4(6) . . . . ?
C7 C6 C5 C4 -179.4(4) . . . . ?
C6 C5 C4 C3 -0.4(6) . . . . ?
C5 C4 C3 C2 -0.1(6) . . . . ?
C9 C10 C11 C12 0.2(6) . . . . ?
N1 N2 C12 C7 -1.4(6) . . . . ?
N1 N2 C12 C11 179.4(3) . . . . ?
C8 C7 C12 N2 -177.4(3) . . . . ?
C6 C7 C12 N2 3.0(6) . . . . ?
C8 C7 C12 C11 1.7(6) . . . . ?
C6 C7 C12 C11 -177.9(3) . . . . ?
C10 C11 C12 N2 177.9(3) . . . . ?
C10 C11 C12 C7 -1.3(6) . . . . ?
N2 N1 C1 C2 -178.2(4) . . . . ?
N2 N1 C1 C6 2.5(6) . . . . ?
C5 C6 C1 N1 179.5(3) . . . . ?
C7 C6 C1 N1 -0.7(5) . . . . ?
C5 C6 C1 C2 0.2(5) . . . . ?
C7 C6 C1 C2 180.0(4) . . . . ?
C4 C3 C2 C1 0.7(6) . . . . ?
N1 C1 C2 C3 179.9(4) . . . . ?
C6 C1 C2 C3 -0.7(6) . . . . ?

_refine_diff_density_max         1.450
_refine_diff_density_min         -1.901
_refine_diff_density_rms         0.197


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
_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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1880031'
_audit_update_record             
;
2018-11-20 deposited with the CCDC.
2019-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
'9,9-Bis(4-aminophenyl)fluorene + 1,4-Diiodotetrafluorobenzene'
_chemical_name_common            
'9,9-Bis(4-aminophenyl)fluorene + 1,4-Diiodotetrafluorobenzene'
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H20 F4 I2 N2'
_chemical_formula_sum            'C31 H20 F4 I2 N2'
_chemical_formula_weight         750.29

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.5700(4)
_cell_length_b                   11.6762(4)
_cell_length_c                   11.7522(4)
_cell_angle_alpha                70.484(2)
_cell_angle_beta                 63.812(2)
_cell_angle_gamma                73.849(2)
_cell_volume                     1326.69(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8943
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      29.99

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.878
_exptl_crystal_F_000             724
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    2.423
_shelx_estimated_absorpt_T_min   0.594
_shelx_estimated_absorpt_T_max   0.811
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5091
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27519
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.992
_diffrn_reflns_theta_max         30.259
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7799
_reflns_number_gt                6406
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0373P)²+1.2868P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7799
_refine_ls_number_parameters     368
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0795
_refine_ls_wR_factor_gt          0.0753
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.82408(2) 0.81752(2) 0.27678(2) 0.01766(6) Uani 1 1 d . . . . .
I2 I 0.78922(2) 1.33088(2) -0.23071(2) 0.02489(6) Uani 1 1 d . . . . .
F1 F 0.69477(17) 1.09918(16) 0.27280(16) 0.0222(4) Uani 1 1 d . . . . .
F2 F 0.68898(18) 1.29601(15) 0.07797(18) 0.0249(4) Uani 1 1 d . . . . .
F3 F 0.90758(19) 1.04670(17) -0.22454(16) 0.0243(4) Uani 1 1 d . . . . .
F4 F 0.92606(19) 0.85314(16) -0.03019(18) 0.0257(4) Uani 1 1 d . . . . .
N1 N 0.4828(3) 1.2651(2) 0.6825(3) 0.0189(5) Uani 1 1 d . . . . .
H1A H 0.429(4) 1.286(4) 0.648(4) 0.035(11) Uiso 1 1 d . . . . .
H1B H 0.454(4) 1.285(3) 0.739(4) 0.017(10) Uiso 1 1 d . . . . .
N2 N 0.6683(3) 0.4611(2) 0.4711(3) 0.0175(5) Uani 1 1 d . . . . .
H2A H 0.605(4) 0.418(3) 0.523(3) 0.018(9) Uiso 1 1 d . . . . .
H2B H 0.728(4) 0.421(4) 0.445(4) 0.031(12) Uiso 1 1 d . . . . .
C1 C 1.1464(3) 0.7884(3) 0.6288(3) 0.0168(5) Uani 1 1 d . . . . .
H1 H 1.233079 0.792675 0.613458 0.020 Uiso 1 1 calc R U . . .
C2 C 1.0678(3) 0.7260(2) 0.7503(3) 0.0153(5) Uani 1 1 d . . . . .
H2 H 1.099810 0.687208 0.818087 0.018 Uiso 1 1 calc R U . . .
C3 C 0.9401(3) 0.7216(2) 0.7709(3) 0.0127(5) Uani 1 1 d . . . . .
C4 C 0.8937(2) 0.7802(2) 0.6704(3) 0.0110(5) Uani 1 1 d . . . . .
C5 C 0.7508(2) 0.7657(2) 0.7171(2) 0.0105(5) Uani 1 1 d . . . . .
C6 C 0.6672(2) 0.8945(2) 0.7136(3) 0.0116(5) Uani 1 1 d . . . . .
C7 C 0.6381(3) 0.9551(2) 0.8096(3) 0.0147(5) Uani 1 1 d . . . . .
H7 H 0.662105 0.912543 0.882267 0.018 Uiso 1 1 calc R U . . .
C8 C 0.5750(3) 1.0755(3) 0.8017(3) 0.0167(5) Uani 1 1 d . . . . .
H8 H 0.556731 1.114346 0.868367 0.020 Uiso 1 1 calc R U . . .
C9 C 0.5383(3) 1.1401(2) 0.6963(3) 0.0149(5) Uani 1 1 d . . . . .
C10 C 0.6900(3) 0.5375(2) 0.5267(3) 0.0126(5) Uani 1 1 d . . . . .
C11 C 0.8156(3) 0.5540(2) 0.4986(3) 0.0139(5) Uani 1 1 d . . . . .
H11 H 0.888409 0.513094 0.439415 0.017 Uiso 1 1 calc R U . . .
C12 C 0.8359(3) 0.6297(2) 0.5561(2) 0.0116(5) Uani 1 1 d . . . . .
H12 H 0.922392 0.638263 0.536578 0.014 Uiso 1 1 calc R U . . .
C13 C 0.7310(3) 0.6932(2) 0.6422(2) 0.0108(5) Uani 1 1 d . . . . .
C14 C 0.5644(3) 1.0804(2) 0.6013(3) 0.0143(5) Uani 1 1 d . . . . .
H14 H 0.537937 1.122314 0.530107 0.017 Uiso 1 1 calc R U . . .
C15 C 0.6294(3) 0.9593(2) 0.6093(3) 0.0130(5) Uani 1 1 d . . . . .
H15 H 0.648039 0.920650 0.542409 0.016 Uiso 1 1 calc R U . . .
C16 C 0.7251(3) 0.6890(2) 0.8580(2) 0.0112(5) Uani 1 1 d . . . . .
C17 C 0.8356(3) 0.6656(2) 0.8873(3) 0.0125(5) Uani 1 1 d . . . . .
C18 C 0.9732(3) 0.8419(2) 0.5492(3) 0.0141(5) Uani 1 1 d . . . . .
H18 H 0.941466 0.881353 0.481361 0.017 Uiso 1 1 calc R U . . .
C19 C 1.1003(3) 0.8449(2) 0.5288(3) 0.0157(5) Uani 1 1 d . . . . .
H19 H 1.156211 0.885858 0.445841 0.019 Uiso 1 1 calc R U . . .
C20 C 0.8328(3) 0.6004(2) 1.0109(3) 0.0159(5) Uani 1 1 d . . . . .
H20 H 0.907113 0.586555 1.031377 0.019 Uiso 1 1 calc R U . . .
C21 C 0.7192(3) 0.5556(2) 1.1042(3) 0.0170(5) Uani 1 1 d . . . . .
H21 H 0.716095 0.509881 1.189019 0.020 Uiso 1 1 calc R U . . .
C22 C 0.6105(3) 0.5771(2) 1.0747(3) 0.0169(5) Uani 1 1 d . . . . .
H22 H 0.533781 0.545394 1.139399 0.020 Uiso 1 1 calc R U . . .
C23 C 0.6121(3) 0.6444(2) 0.9517(3) 0.0148(5) Uani 1 1 d . . . . .
H23 H 0.536917 0.659542 0.932192 0.018 Uiso 1 1 calc R U . . .
C24 C 0.6057(3) 0.6807(2) 0.6639(3) 0.0121(5) Uani 1 1 d . . . . .
H24 H 0.532636 0.726062 0.718204 0.015 Uiso 1 1 calc R U . . .
C25 C 0.5846(3) 0.6046(2) 0.6089(3) 0.0134(5) Uani 1 1 d . . . . .
H25 H 0.498010 0.597633 0.626887 0.016 Uiso 1 1 calc R U . . .
C26 C 0.8089(3) 0.9702(2) 0.1270(3) 0.0150(5) Uani 1 1 d . . . . .
C27 C 0.8629(3) 0.9602(3) -0.0017(3) 0.0161(5) Uani 1 1 d . . . . .
C28 C 0.8550(3) 1.0620(3) -0.1022(3) 0.0165(5) Uani 1 1 d . . . . .
C29 C 0.7965(3) 1.1774(3) -0.0792(3) 0.0176(6) Uani 1 1 d . . . . .
C30 C 0.7488(3) 1.0847(3) 0.1504(3) 0.0155(5) Uani 1 1 d . . . . .
C31 C 0.7444(3) 1.1863(3) 0.0490(3) 0.0175(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C26 2.076(3) . ?
I2 C29 2.075(3) . ?
F1 C30 1.342(3) . ?
F2 C31 1.346(3) . ?
F3 C28 1.345(3) . ?
F4 C27 1.328(3) . ?
N1 C9 1.408(4) . ?
N1 H1A 0.82(5) . ?
N1 H1B 0.69(4) . ?
N2 C10 1.395(4) . ?
N2 H2A 0.88(4) . ?
N2 H2B 0.72(4) . ?
C1 C2 1.388(4) . ?
C1 C19 1.393(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.401(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.402(4) . ?
C3 C17 1.464(4) . ?
C4 C18 1.386(4) . ?
C4 C5 1.536(4) . ?
C5 C13 1.525(4) . ?
C5 C16 1.535(4) . ?
C5 C6 1.544(4) . ?
C6 C15 1.391(4) . ?
C6 C7 1.397(4) . ?
C7 C8 1.386(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(4) . ?
C8 H8 0.9500 . ?
C9 C14 1.389(4) . ?
C10 C11 1.396(4) . ?
C10 C25 1.402(4) . ?
C11 C12 1.395(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.401(4) . ?
C12 H12 0.9500 . ?
C13 C24 1.398(4) . ?
C14 C15 1.398(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C23 1.385(4) . ?
C16 C17 1.399(4) . ?
C17 C20 1.388(4) . ?
C18 C19 1.390(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.389(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.384(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.391(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 1.383(4) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C30 1.380(4) . ?
C26 C27 1.392(4) . ?
C27 C28 1.382(4) . ?
C28 C29 1.386(4) . ?
C29 C31 1.382(4) . ?
C30 C31 1.380(4) . ?

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
C9 N1 H1A 114(3) . . ?
C9 N1 H1B 116(3) . . ?
H1A N1 H1B 107(4) . . ?
C10 N2 H2A 115(2) . . ?
C10 N2 H2B 109(3) . . ?
H2A N2 H2B 110(4) . . ?
C2 C1 C19 121.0(3) . . ?
C2 C1 H1 119.5 . . ?
C19 C1 H1 119.5 . . ?
C1 C2 C3 118.5(3) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 C17 130.8(3) . . ?
C4 C3 C17 109.1(2) . . ?
C18 C4 C3 120.9(2) . . ?
C18 C4 C5 128.5(2) . . ?
C3 C4 C5 110.6(2) . . ?
C13 C5 C16 109.0(2) . . ?
C13 C5 C4 113.2(2) . . ?
C16 C5 C4 100.7(2) . . ?
C13 C5 C6 113.4(2) . . ?
C16 C5 C6 111.5(2) . . ?
C4 C5 C6 108.4(2) . . ?
C15 C6 C7 117.5(2) . . ?
C15 C6 C5 121.7(2) . . ?
C7 C6 C5 120.5(2) . . ?
C8 C7 C6 121.7(3) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 120.4(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C14 C9 C8 118.6(2) . . ?
C14 C9 N1 120.5(3) . . ?
C8 C9 N1 120.8(3) . . ?
N2 C10 C11 121.6(3) . . ?
N2 C10 C25 120.4(3) . . ?
C11 C10 C25 117.9(2) . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 121.2(2) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C24 C13 C12 117.0(2) . . ?
C24 C13 C5 120.7(2) . . ?
C12 C13 C5 122.2(2) . . ?
C9 C14 C15 120.6(3) . . ?
C9 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C6 C15 C14 121.2(2) . . ?
C6 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C23 C16 C17 120.2(2) . . ?
C23 C16 C5 128.7(2) . . ?
C17 C16 C5 111.1(2) . . ?
C20 C17 C16 120.7(2) . . ?
C20 C17 C3 130.8(3) . . ?
C16 C17 C3 108.5(2) . . ?
C4 C18 C19 118.8(3) . . ?
C4 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C18 C19 C1 120.7(3) . . ?
C18 C19 H19 119.7 . . ?
C1 C19 H19 119.7 . . ?
C17 C20 C21 118.7(3) . . ?
C17 C20 H20 120.6 . . ?
C21 C20 H20 120.6 . . ?
C22 C21 C20 120.5(3) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 121.0(3) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C16 C23 C22 118.8(3) . . ?
C16 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C25 C24 C13 122.1(2) . . ?
C25 C24 H24 118.9 . . ?
C13 C24 H24 118.9 . . ?
C24 C25 C10 120.6(2) . . ?
C24 C25 H25 119.7 . . ?
C10 C25 H25 119.7 . . ?
C30 C26 C27 117.8(2) . . ?
C30 C26 I1 121.8(2) . . ?
C27 C26 I1 120.3(2) . . ?
F4 C27 C28 119.0(2) . . ?
F4 C27 C26 120.3(2) . . ?
C28 C27 C26 120.6(3) . . ?
F3 C28 C27 118.1(3) . . ?
F3 C28 C29 120.3(2) . . ?
C27 C28 C29 121.6(3) . . ?
C31 C29 C28 117.1(3) . . ?
C31 C29 I2 121.3(2) . . ?
C28 C29 I2 121.5(2) . . ?
F1 C30 C31 118.8(2) . . ?
F1 C30 C26 120.2(2) . . ?
C31 C30 C26 121.0(3) . . ?
F2 C31 C30 118.0(3) . . ?
F2 C31 C29 120.3(3) . . ?
C30 C31 C29 121.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C19 C1 C2 C3 -0.4(4) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C1 C2 C3 C17 -178.8(3) . . . . ?
C2 C3 C4 C18 0.8(4) . . . . ?
C17 C3 C4 C18 179.4(2) . . . . ?
C2 C3 C4 C5 -178.5(2) . . . . ?
C17 C3 C4 C5 0.1(3) . . . . ?
C18 C4 C5 C13 64.0(3) . . . . ?
C3 C4 C5 C13 -116.8(2) . . . . ?
C18 C4 C5 C16 -179.8(3) . . . . ?
C3 C4 C5 C16 -0.6(3) . . . . ?
C18 C4 C5 C6 -62.7(3) . . . . ?
C3 C4 C5 C6 116.5(2) . . . . ?
C13 C5 C6 C15 -28.7(3) . . . . ?
C16 C5 C6 C15 -152.1(2) . . . . ?
C4 C5 C6 C15 97.9(3) . . . . ?
C13 C5 C6 C7 157.9(2) . . . . ?
C16 C5 C6 C7 34.4(3) . . . . ?
C4 C5 C6 C7 -75.6(3) . . . . ?
C15 C6 C7 C8 -0.6(4) . . . . ?
C5 C6 C7 C8 173.2(2) . . . . ?
C6 C7 C8 C9 0.2(4) . . . . ?
C7 C8 C9 C14 1.0(4) . . . . ?
C7 C8 C9 N1 -175.4(3) . . . . ?
N2 C10 C11 C12 -179.3(2) . . . . ?
C25 C10 C11 C12 3.4(4) . . . . ?
C10 C11 C12 C13 -1.1(4) . . . . ?
C11 C12 C13 C24 -2.2(4) . . . . ?
C11 C12 C13 C5 173.5(2) . . . . ?
C16 C5 C13 C24 74.6(3) . . . . ?
C4 C5 C13 C24 -174.2(2) . . . . ?
C6 C5 C13 C24 -50.2(3) . . . . ?
C16 C5 C13 C12 -101.0(3) . . . . ?
C4 C5 C13 C12 10.2(3) . . . . ?
C6 C5 C13 C12 134.2(2) . . . . ?
C8 C9 C14 C15 -1.7(4) . . . . ?
N1 C9 C14 C15 174.7(3) . . . . ?
C7 C6 C15 C14 -0.2(4) . . . . ?
C5 C6 C15 C14 -173.8(2) . . . . ?
C9 C14 C15 C6 1.3(4) . . . . ?
C13 C5 C16 C23 -59.9(3) . . . . ?
C4 C5 C16 C23 -179.2(3) . . . . ?
C6 C5 C16 C23 66.0(3) . . . . ?
C13 C5 C16 C17 120.1(2) . . . . ?
C4 C5 C16 C17 0.8(3) . . . . ?
C6 C5 C16 C17 -114.0(2) . . . . ?
C23 C16 C17 C20 -1.7(4) . . . . ?
C5 C16 C17 C20 178.3(2) . . . . ?
C23 C16 C17 C3 179.2(2) . . . . ?
C5 C16 C17 C3 -0.8(3) . . . . ?
C2 C3 C17 C20 -0.2(5) . . . . ?
C4 C3 C17 C20 -178.6(3) . . . . ?
C2 C3 C17 C16 178.8(3) . . . . ?
C4 C3 C17 C16 0.4(3) . . . . ?
C3 C4 C18 C19 -0.1(4) . . . . ?
C5 C4 C18 C19 179.0(2) . . . . ?
C4 C18 C19 C1 -0.8(4) . . . . ?
C2 C1 C19 C18 1.1(4) . . . . ?
C16 C17 C20 C21 1.8(4) . . . . ?
C3 C17 C20 C21 -179.3(3) . . . . ?
C17 C20 C21 C22 -0.8(4) . . . . ?
C20 C21 C22 C23 -0.4(4) . . . . ?
C17 C16 C23 C22 0.5(4) . . . . ?
C5 C16 C23 C22 -179.5(2) . . . . ?
C21 C22 C23 C16 0.6(4) . . . . ?
C12 C13 C24 C25 3.2(4) . . . . ?
C5 C13 C24 C25 -172.6(2) . . . . ?
C13 C24 C25 C10 -0.9(4) . . . . ?
N2 C10 C25 C24 -179.8(2) . . . . ?
C11 C10 C25 C24 -2.5(4) . . . . ?
C30 C26 C27 F4 177.5(3) . . . . ?
I1 C26 C27 F4 -0.8(4) . . . . ?
C30 C26 C27 C28 -0.5(4) . . . . ?
I1 C26 C27 C28 -178.9(2) . . . . ?
F4 C27 C28 F3 2.7(4) . . . . ?
C26 C27 C28 F3 -179.2(3) . . . . ?
F4 C27 C28 C29 -176.5(3) . . . . ?
C26 C27 C28 C29 1.6(4) . . . . ?
F3 C28 C29 C31 179.9(2) . . . . ?
C27 C28 C29 C31 -0.9(4) . . . . ?
F3 C28 C29 I2 -0.8(4) . . . . ?
C27 C28 C29 I2 178.3(2) . . . . ?
C27 C26 C30 F1 179.8(2) . . . . ?
I1 C26 C30 F1 -1.9(4) . . . . ?
C27 C26 C30 C31 -1.1(4) . . . . ?
I1 C26 C30 C31 177.2(2) . . . . ?
F1 C30 C31 F2 1.8(4) . . . . ?
C26 C30 C31 F2 -177.3(3) . . . . ?
F1 C30 C31 C29 -179.1(3) . . . . ?
C26 C30 C31 C29 1.9(4) . . . . ?
C28 C29 C31 F2 178.4(3) . . . . ?
I2 C29 C31 F2 -0.9(4) . . . . ?
C28 C29 C31 C30 -0.8(4) . . . . ?
I2 C29 C31 C30 180.0(2) . . . . ?

_refine_diff_density_max         1.910
_refine_diff_density_min         -1.779
_refine_diff_density_rms         0.125


_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. 
# 
#######################################################################


####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1880028'
_audit_update_record             
;
2018-11-20 deposited with the CCDC.
2019-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
'Diphenylvinyl biphenyl + 1,4-Diiodotetrafluorobenzene'
_chemical_name_common            
'Diphenylvinyl biphenyl + 1,4-Diiodotetrafluorobenzene'
_chemical_melting_point          ?
_chemical_formula_moiety         'C46 H30 F4 I2'
_chemical_formula_sum            'C46 H30 F4 I2'
_chemical_formula_weight         912.50

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'
I I -0.4742 1.8119 '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                   13.9639(5)
_cell_length_b                   9.2151(3)
_cell_length_c                   28.0322(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.6600(10)
_cell_angle_gamma                90
_cell_volume                     3566.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9932
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      29.90


_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_F_000             1792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.819
_shelx_estimated_absorpt_T_min   0.701
_shelx_estimated_absorpt_T_max   0.868
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5173
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35790
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.234
_diffrn_reflns_theta_max         27.878
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8468
_reflns_number_gt                7423
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0237P)²+3.5192P] 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         8468
_refine_ls_number_parameters     469
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0670
_refine_ls_wR_factor_gt          0.0642
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.40798(2) -0.96005(2) 0.09580(2) 0.02246(5) Uani 1 1 d . . . . .
I2 I 0.77330(2) -1.30411(2) -0.00452(2) 0.02383(5) Uani 1 1 d . . . . .
F1 F 0.77041(10) -1.01099(16) 0.05687(5) 0.0219(3) Uani 1 1 d . . . . .
F2 F 0.40905(11) -1.24402(17) 0.02960(5) 0.0259(3) Uani 1 1 d . . . . .
F3 F 0.62821(11) -0.87601(15) 0.09289(5) 0.0227(3) Uani 1 1 d . . . . .
F4 F 0.55042(11) -1.37560(15) -0.00743(5) 0.0259(3) Uani 1 1 d . . . . .
C1 C 0.90597(18) 1.4051(3) 0.45801(9) 0.0176(5) Uani 1 1 d . . . . .
H1 H 0.909883 1.498393 0.472595 0.021 Uiso 1 1 calc R U . . .
C2 C 0.98060(18) 1.3547(3) 0.43505(9) 0.0179(5) Uani 1 1 d . . . . .
H2 H 1.035527 1.414387 0.433501 0.022 Uiso 1 1 calc R U . . .
C3 C 0.97568(17) 1.2174(2) 0.41423(9) 0.0152(5) Uani 1 1 d . . . . .
H3 H 1.027560 1.183975 0.398755 0.018 Uiso 1 1 calc R U . . .
C4 C 0.89502(17) 1.1275(2) 0.41581(8) 0.0120(4) Uani 1 1 d . . . . .
C5 C 0.89045(17) 0.9813(2) 0.39256(8) 0.0125(5) Uani 1 1 d . . . . .
C6 C 0.80401(17) 0.9198(2) 0.37610(8) 0.0119(4) Uani 1 1 d . . . . .
H7 H 0.748931 0.976551 0.380014 0.014 Uiso 1 1 calc R U . . .
C7 C 0.78261(16) 0.7775(2) 0.35296(8) 0.0114(4) Uani 1 1 d . . . . .
C8 C 0.69451(17) 0.7602(2) 0.32230(8) 0.0126(5) Uani 1 1 d . . . . .
H8 H 0.650524 0.839415 0.317604 0.015 Uiso 1 1 calc R U . . .
C9 C 0.66985(16) 0.6301(2) 0.29857(8) 0.0122(4) Uani 1 1 d . . . . .
H9 H 0.609899 0.622496 0.277619 0.015 Uiso 1 1 calc R U . . .
C10 C 0.73191(16) 0.5096(2) 0.30499(8) 0.0107(4) Uani 1 1 d . . . . .
C11 C 0.70740(16) 0.3725(2) 0.27789(8) 0.0110(4) Uani 1 1 d . . . . .
C12 C 0.75207(16) 0.2402(2) 0.29276(8) 0.0125(5) Uani 1 1 d . . . . .
H12 H 0.798912 0.237562 0.321081 0.015 Uiso 1 1 calc R U . . .
C13 C 0.72928(16) 0.1132(2) 0.26698(8) 0.0131(5) Uani 1 1 d . . . . .
H13 H 0.762712 0.026211 0.277172 0.016 Uiso 1 1 calc R U . . .
C14 C 0.65820(16) 0.1112(2) 0.22639(8) 0.0125(4) Uani 1 1 d . . . . .
C15 C 0.62214(17) -0.0222(2) 0.20057(8) 0.0131(5) Uani 1 1 d . . . . .
H15 H 0.554263 -0.024316 0.189936 0.016 Uiso 1 1 calc R U . . .
C16 C 0.67039(16) -0.1412(2) 0.18974(8) 0.0114(4) Uani 1 1 d . . . . .
C17 C 0.77823(16) -0.1486(2) 0.19639(8) 0.0114(4) Uani 1 1 d . . . . .
C18 C 0.83118(17) -0.0372(2) 0.17909(8) 0.0147(5) Uani 1 1 d . . . . .
H18 H 0.797964 0.043633 0.163350 0.018 Uiso 1 1 calc R U . . .
C19 C 0.93141(18) -0.0422(3) 0.18447(9) 0.0177(5) Uani 1 1 d . . . . .
H19 H 0.966391 0.034614 0.172460 0.021 Uiso 1 1 calc R U . . .
C20 C 0.98044(18) -0.1595(3) 0.20739(9) 0.0181(5) Uani 1 1 d . . . . .
H20 H 1.049183 -0.162872 0.211464 0.022 Uiso 1 1 calc R U . . .
C21 C 0.50452(19) -0.4934(3) 0.11844(9) 0.0184(5) Uani 1 1 d . . . . .
H21 H 0.466930 -0.568937 0.101839 0.022 Uiso 1 1 calc R U . . .
C22 C 0.59988(19) -0.4732(2) 0.11171(9) 0.0181(5) Uani 1 1 d . . . . .
H22 H 0.627981 -0.535644 0.090680 0.022 Uiso 1 1 calc R U . . .
C23 C 0.65480(18) -0.3614(2) 0.13569(8) 0.0149(5) Uani 1 1 d . . . . .
H23 H 0.720303 -0.348969 0.131034 0.018 Uiso 1 1 calc R U . . .
C24 C 0.61473(16) -0.2673(2) 0.16647(8) 0.0112(4) Uani 1 1 d . . . . .
C25 C 0.82889(17) -0.2679(2) 0.21832(8) 0.0146(5) Uani 1 1 d . . . . .
H25 H 0.794173 -0.346921 0.229183 0.017 Uiso 1 1 calc R U . . .
C26 C 0.92904(18) -0.2720(3) 0.22437(9) 0.0175(5) Uani 1 1 d . . . . .
H26 H 0.962678 -0.352248 0.240230 0.021 Uiso 1 1 calc R U . . .
C27 C 0.63867(17) 0.3709(2) 0.23627(8) 0.0143(5) Uani 1 1 d . . . . .
H27 H 0.608782 0.459215 0.224614 0.017 Uiso 1 1 calc R U . . .
C28 C 0.61309(17) 0.2428(2) 0.21153(8) 0.0143(5) Uani 1 1 d . . . . .
H28 H 0.564138 0.244505 0.184051 0.017 Uiso 1 1 calc R U . . .
C29 C 0.82528(18) 1.3178(3) 0.45952(9) 0.0177(5) Uani 1 1 d . . . . .
H29 H 0.773338 1.352500 0.474713 0.021 Uiso 1 1 calc R U . . .
C30 C 0.81998(18) 1.1801(2) 0.43894(8) 0.0149(5) Uani 1 1 d . . . . .
H30 H 0.764808 1.121037 0.440629 0.018 Uiso 1 1 calc R U . . .
C31 C 0.98597(17) 0.9181(2) 0.38527(8) 0.0135(5) Uani 1 1 d . . . . .
C32 C 1.05524(18) 0.8820(3) 0.42469(9) 0.0189(5) Uani 1 1 d . . . . .
H32 H 1.039937 0.890179 0.456472 0.023 Uiso 1 1 calc R U . . .
C33 C 1.14629(19) 0.8344(3) 0.41775(10) 0.0226(6) Uani 1 1 d . . . . .
H33 H 1.192788 0.808540 0.444733 0.027 Uiso 1 1 calc R U . . .
C34 C 1.16962(18) 0.8244(3) 0.37151(10) 0.0204(5) Uani 1 1 d . . . . .
H34 H 1.232703 0.794789 0.366809 0.024 Uiso 1 1 calc R U . . .
C35 C 1.10071(18) 0.8576(3) 0.33226(9) 0.0195(5) Uani 1 1 d . . . . .
H35 H 1.116022 0.848571 0.300503 0.023 Uiso 1 1 calc R U . . .
C36 C 1.00897(18) 0.9041(3) 0.33915(9) 0.0170(5) Uani 1 1 d . . . . .
H36 H 0.961849 0.926455 0.312037 0.020 Uiso 1 1 calc R U . . .
C37 C 0.84280(17) 0.6555(2) 0.36080(8) 0.0136(5) Uani 1 1 d . . . . .
H37 H 0.901950 0.662369 0.382411 0.016 Uiso 1 1 calc R U . . .
C38 C 0.81778(17) 0.5252(2) 0.33767(8) 0.0127(5) Uani 1 1 d . . . . .
H38 H 0.859875 0.444302 0.344099 0.015 Uiso 1 1 calc R U . . .
C39 C 0.51888(17) -0.2917(2) 0.17380(8) 0.0140(5) Uani 1 1 d . . . . .
H39 H 0.490922 -0.231676 0.195569 0.017 Uiso 1 1 calc R U . . .
C40 C 0.46433(18) -0.4027(3) 0.14959(9) 0.0184(5) Uani 1 1 d . . . . .
H40 H 0.399049 -0.416590 0.154410 0.022 Uiso 1 1 calc R U . . .
C41 C 0.68180(17) -1.0709(3) 0.05014(8) 0.0154(5) Uani 1 1 d . . . . .
C42 C 0.60800(18) -1.0016(2) 0.06910(8) 0.0153(5) Uani 1 1 d . . . . .
C43 C 0.51522(18) -1.0585(3) 0.06350(8) 0.0156(5) Uani 1 1 d . . . . .
C44 C 0.49792(18) -1.1849(3) 0.03736(9) 0.0167(5) Uani 1 1 d . . . . .
C45 C 0.66432(17) -1.1987(3) 0.02458(8) 0.0151(5) Uani 1 1 d . . . . .
C46 C 0.57115(18) -1.2533(3) 0.01803(9) 0.0171(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C43 2.072(2) . ?
I2 C45 2.073(2) . ?
F1 C41 1.342(3) . ?
F2 C44 1.343(3) . ?
F3 C42 1.345(3) . ?
F4 C46 1.342(3) . ?
C1 C2 1.385(4) . ?
C1 C29 1.390(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(3) . ?
C3 H3 0.9500 . ?
C4 C30 1.399(3) . ?
C4 C5 1.494(3) . ?
C5 C6 1.350(3) . ?
C5 C31 1.497(3) . ?
C6 C7 1.474(3) . ?
C6 H7 0.9500 . ?
C7 C8 1.400(3) . ?
C7 C37 1.401(3) . ?
C8 C9 1.390(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.403(3) . ?
C9 H9 0.9500 . ?
C10 C38 1.403(3) . ?
C10 C11 1.488(3) . ?
C11 C27 1.395(3) . ?
C11 C12 1.404(3) . ?
C12 C13 1.387(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.393(3) . ?
C13 H13 0.9500 . ?
C14 C28 1.401(3) . ?
C14 C15 1.475(3) . ?
C15 C16 1.346(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.491(3) . ?
C16 C24 1.492(3) . ?
C17 C18 1.394(3) . ?
C17 C25 1.399(3) . ?
C18 C19 1.386(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(3) . ?
C19 H19 0.9500 . ?
C20 C26 1.385(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.385(4) . ?
C21 C40 1.387(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.395(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.398(3) . ?
C23 H23 0.9500 . ?
C24 C39 1.403(3) . ?
C25 C26 1.384(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.388(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.392(3) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C36 1.384(3) . ?
C31 C32 1.395(3) . ?
C32 C33 1.386(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.386(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.382(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.392(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 C38 1.384(3) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 C40 1.390(3) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 C45 1.381(3) . ?
C41 C42 1.384(3) . ?
C42 C43 1.384(3) . ?
C43 C44 1.378(3) . ?
C44 C46 1.380(4) . ?
C45 C46 1.381(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 C29 119.4(2) . . ?
C2 C1 H1 120.3 . . ?
C29 C1 H1 120.3 . . ?
C1 C2 C3 120.5(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 120.8(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C30 C4 C3 118.1(2) . . ?
C30 C4 C5 121.9(2) . . ?
C3 C4 C5 120.0(2) . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 C31 124.0(2) . . ?
C4 C5 C31 115.5(2) . . ?
C5 C6 C7 129.5(2) . . ?
C5 C6 H7 115.3 . . ?
C7 C6 H7 115.3 . . ?
C8 C7 C37 117.2(2) . . ?
C8 C7 C6 118.2(2) . . ?
C37 C7 C6 124.6(2) . . ?
C9 C8 C7 121.6(2) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 121.2(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C38 C10 C9 116.9(2) . . ?
C38 C10 C11 122.0(2) . . ?
C9 C10 C11 121.1(2) . . ?
C27 C11 C12 117.3(2) . . ?
C27 C11 C10 120.8(2) . . ?
C12 C11 C10 121.89(19) . . ?
C13 C12 C11 121.4(2) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 121.1(2) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C13 C14 C28 117.6(2) . . ?
C13 C14 C15 124.1(2) . . ?
C28 C14 C15 118.1(2) . . ?
C16 C15 C14 130.1(2) . . ?
C16 C15 H15 115.0 . . ?
C14 C15 H15 115.0 . . ?
C15 C16 C17 122.6(2) . . ?
C15 C16 C24 119.2(2) . . ?
C17 C16 C24 117.99(19) . . ?
C18 C17 C25 118.2(2) . . ?
C18 C17 C16 120.1(2) . . ?
C25 C17 C16 121.7(2) . . ?
C19 C18 C17 121.2(2) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C20 C19 C18 119.8(2) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C26 C20 C19 119.9(2) . . ?
C26 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C22 C21 C40 119.5(2) . . ?
C22 C21 H21 120.2 . . ?
C40 C21 H21 120.2 . . ?
C21 C22 C23 120.3(2) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C24 120.9(2) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C23 C24 C39 118.1(2) . . ?
C23 C24 C16 121.5(2) . . ?
C39 C24 C16 120.4(2) . . ?
C26 C25 C17 120.7(2) . . ?
C26 C25 H25 119.7 . . ?
C17 C25 H25 119.7 . . ?
C25 C26 C20 120.3(2) . . ?
C25 C26 H26 119.9 . . ?
C20 C26 H26 119.9 . . ?
C28 C27 C11 121.3(2) . . ?
C28 C27 H27 119.3 . . ?
C11 C27 H27 119.3 . . ?
C27 C28 C14 121.2(2) . . ?
C27 C28 H28 119.4 . . ?
C14 C28 H28 119.4 . . ?
C1 C29 C30 120.5(2) . . ?
C1 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C29 C30 C4 120.7(2) . . ?
C29 C30 H30 119.6 . . ?
C4 C30 H30 119.6 . . ?
C36 C31 C32 119.1(2) . . ?
C36 C31 C5 120.0(2) . . ?
C32 C31 C5 120.7(2) . . ?
C33 C32 C31 120.4(2) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C32 C33 C34 120.1(2) . . ?
C32 C33 H33 119.9 . . ?
C34 C33 H33 119.9 . . ?
C35 C34 C33 119.7(2) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C34 C35 C36 120.2(2) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C31 C36 C35 120.4(2) . . ?
C31 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?
C38 C37 C7 121.3(2) . . ?
C38 C37 H37 119.4 . . ?
C7 C37 H37 119.4 . . ?
C37 C38 C10 121.7(2) . . ?
C37 C38 H38 119.1 . . ?
C10 C38 H38 119.1 . . ?
C40 C39 C24 120.7(2) . . ?
C40 C39 H39 119.6 . . ?
C24 C39 H39 119.6 . . ?
C21 C40 C39 120.5(2) . . ?
C21 C40 H40 119.8 . . ?
C39 C40 H40 119.8 . . ?
F1 C41 C45 120.7(2) . . ?
F1 C41 C42 118.7(2) . . ?
C45 C41 C42 120.6(2) . . ?
F3 C42 C43 120.3(2) . . ?
F3 C42 C41 118.3(2) . . ?
C43 C42 C41 121.3(2) . . ?
C44 C43 C42 117.8(2) . . ?
C44 C43 I1 121.47(18) . . ?
C42 C43 I1 120.69(17) . . ?
F2 C44 C43 120.9(2) . . ?
F2 C44 C46 118.2(2) . . ?
C43 C44 C46 120.9(2) . . ?
C41 C45 C46 118.0(2) . . ?
C41 C45 I2 121.39(18) . . ?
C46 C45 I2 120.62(18) . . ?
F4 C46 C44 118.6(2) . . ?
F4 C46 C45 120.0(2) . . ?
C44 C46 C45 121.3(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
C29 C1 C2 C3 -0.9(3) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C30 -0.1(3) . . . . ?
C2 C3 C4 C5 179.1(2) . . . . ?
C30 C4 C5 C6 26.4(3) . . . . ?
C3 C4 C5 C6 -152.7(2) . . . . ?
C30 C4 C5 C31 -158.9(2) . . . . ?
C3 C4 C5 C31 22.0(3) . . . . ?
C4 C5 C6 C7 -179.0(2) . . . . ?
C31 C5 C6 C7 6.8(4) . . . . ?
C5 C6 C7 C8 -154.7(2) . . . . ?
C5 C6 C7 C37 27.8(4) . . . . ?
C37 C7 C8 C9 -3.3(3) . . . . ?
C6 C7 C8 C9 179.0(2) . . . . ?
C7 C8 C9 C10 1.0(4) . . . . ?
C8 C9 C10 C38 2.3(3) . . . . ?
C8 C9 C10 C11 -177.2(2) . . . . ?
C38 C10 C11 C27 -161.1(2) . . . . ?
C9 C10 C11 C27 18.4(3) . . . . ?
C38 C10 C11 C12 18.7(3) . . . . ?
C9 C10 C11 C12 -161.8(2) . . . . ?
C27 C11 C12 C13 0.4(3) . . . . ?
C10 C11 C12 C13 -179.4(2) . . . . ?
C11 C12 C13 C14 -2.7(4) . . . . ?
C12 C13 C14 C28 2.3(3) . . . . ?
C12 C13 C14 C15 -172.6(2) . . . . ?
C13 C14 C15 C16 -40.1(4) . . . . ?
C28 C14 C15 C16 145.1(3) . . . . ?
C14 C15 C16 C17 -9.9(4) . . . . ?
C14 C15 C16 C24 175.1(2) . . . . ?
C15 C16 C17 C18 -48.5(3) . . . . ?
C24 C16 C17 C18 126.5(2) . . . . ?
C15 C16 C17 C25 133.8(2) . . . . ?
C24 C16 C17 C25 -51.2(3) . . . . ?
C25 C17 C18 C19 -1.6(3) . . . . ?
C16 C17 C18 C19 -179.4(2) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C18 C19 C20 C26 0.7(4) . . . . ?
C40 C21 C22 C23 -0.7(4) . . . . ?
C21 C22 C23 C24 -0.6(3) . . . . ?
C22 C23 C24 C39 2.1(3) . . . . ?
C22 C23 C24 C16 -175.8(2) . . . . ?
C15 C16 C24 C23 150.9(2) . . . . ?
C17 C16 C24 C23 -24.3(3) . . . . ?
C15 C16 C24 C39 -27.0(3) . . . . ?
C17 C16 C24 C39 157.8(2) . . . . ?
C18 C17 C25 C26 2.6(3) . . . . ?
C16 C17 C25 C26 -179.6(2) . . . . ?
C17 C25 C26 C20 -2.0(4) . . . . ?
C19 C20 C26 C25 0.3(4) . . . . ?
C12 C11 C27 C28 2.2(3) . . . . ?
C10 C11 C27 C28 -178.0(2) . . . . ?
C11 C27 C28 C14 -2.6(4) . . . . ?
C13 C14 C28 C27 0.3(4) . . . . ?
C15 C14 C28 C27 175.5(2) . . . . ?
C2 C1 C29 C30 1.1(3) . . . . ?
C1 C29 C30 C4 -0.9(3) . . . . ?
C3 C4 C30 C29 0.3(3) . . . . ?
C5 C4 C30 C29 -178.8(2) . . . . ?
C6 C5 C31 C36 63.9(3) . . . . ?
C4 C5 C31 C36 -110.6(2) . . . . ?
C6 C5 C31 C32 -120.6(3) . . . . ?
C4 C5 C31 C32 64.9(3) . . . . ?
C36 C31 C32 C33 0.7(4) . . . . ?
C5 C31 C32 C33 -174.9(2) . . . . ?
C31 C32 C33 C34 1.0(4) . . . . ?
C32 C33 C34 C35 -2.1(4) . . . . ?
C33 C34 C35 C36 1.5(4) . . . . ?
C32 C31 C36 C35 -1.3(3) . . . . ?
C5 C31 C36 C35 174.3(2) . . . . ?
C34 C35 C36 C31 0.2(4) . . . . ?
C8 C7 C37 C38 2.5(3) . . . . ?
C6 C7 C37 C38 -180.0(2) . . . . ?
C7 C37 C38 C10 0.8(4) . . . . ?
C9 C10 C38 C37 -3.1(3) . . . . ?
C11 C10 C38 C37 176.4(2) . . . . ?
C23 C24 C39 C40 -2.5(3) . . . . ?
C16 C24 C39 C40 175.4(2) . . . . ?
C22 C21 C40 C39 0.3(4) . . . . ?
C24 C39 C40 C21 1.4(4) . . . . ?
F1 C41 C42 F3 0.9(3) . . . . ?
C45 C41 C42 F3 -178.7(2) . . . . ?
F1 C41 C42 C43 -179.7(2) . . . . ?
C45 C41 C42 C43 0.6(4) . . . . ?
F3 C42 C43 C44 177.8(2) . . . . ?
C41 C42 C43 C44 -1.5(3) . . . . ?
F3 C42 C43 I1 -4.5(3) . . . . ?
C41 C42 C43 I1 176.11(17) . . . . ?
C42 C43 C44 F2 -178.4(2) . . . . ?
I1 C43 C44 F2 3.9(3) . . . . ?
C42 C43 C44 C46 0.9(3) . . . . ?
I1 C43 C44 C46 -176.76(18) . . . . ?
F1 C41 C45 C46 -178.7(2) . . . . ?
C42 C41 C45 C46 0.9(3) . . . . ?
F1 C41 C45 I2 0.1(3) . . . . ?
C42 C41 C45 I2 179.66(17) . . . . ?
F2 C44 C46 F4 -0.2(3) . . . . ?
C43 C44 C46 F4 -179.5(2) . . . . ?
F2 C44 C46 C45 -180.0(2) . . . . ?
C43 C44 C46 C45 0.7(4) . . . . ?
C41 C45 C46 F4 178.6(2) . . . . ?
I2 C45 C46 F4 -0.1(3) . . . . ?
C41 C45 C46 C44 -1.6(4) . . . . ?
I2 C45 C46 C44 179.66(18) . . . . ?

_refine_diff_density_max         0.818
_refine_diff_density_min         -1.087
_refine_diff_density_rms         0.096


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
_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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1880027'
_audit_update_record             
;
2018-11-20 deposited with the CCDC.
2019-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'Benzocinnoline + 1,4-Diiodotetrafluorobenzene'
_chemical_name_common            'Benzocinnoline + 1,4-Diiodotetrafluorobenzene'
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H16 F4 I2 N4'
_chemical_formula_sum            'C30 H16 F4 I2 N4'
_chemical_formula_weight         762.27

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   26.714(9)
_cell_length_b                   13.423(4)
_cell_length_c                   7.556(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.82(2)
_cell_angle_gamma                90
_cell_volume                     2684.1(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9081
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      28.77

_exptl_crystal_description       Rod
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.886
_exptl_crystal_F_000             1464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    2.399
_shelx_estimated_absorpt_T_min   0.645
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.4668
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40215
_diffrn_reflns_av_unetI/netI     0.1811
_diffrn_reflns_av_R_equivalents  0.1748
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.161
_diffrn_reflns_theta_max         30.421
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8066
_reflns_number_gt                3066
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0742P)²] 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         8066
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2393
_refine_ls_R_factor_gt           0.0909
_refine_ls_wR_factor_ref         0.2157
_refine_ls_wR_factor_gt          0.1611
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.84323(3) 0.91066(5) 0.60841(8) 0.0604(2) Uani 1 1 d . . . . .
I2 I 0.67242(3) 0.52214(5) 0.36761(9) 0.0698(3) Uani 1 1 d . . . . .
F1 F 0.8530(2) 0.6711(4) 0.6411(7) 0.0739(16) Uani 1 1 d . . . . .
F2 F 0.7876(2) 0.5257(4) 0.5517(8) 0.0771(17) Uani 1 1 d . . . . .
F3 F 0.6653(2) 0.7609(5) 0.3129(9) 0.0839(17) Uani 1 1 d . . . . .
F4 F 0.7310(2) 0.9059(4) 0.4054(8) 0.0782(17) Uani 1 1 d . . . . .
N1 N 0.8995(3) 1.0888(6) 0.7111(10) 0.064(2) Uani 1 1 d . . . . .
N2 N 0.9446(3) 1.0906(6) 0.6650(11) 0.064(2) Uani 1 1 d . . . . .
N3 N 0.5971(4) 0.3606(7) 0.2895(11) 0.071(2) Uani 1 1 d . . . . .
N4 N 0.5553(4) 0.3930(6) 0.2073(12) 0.067(2) Uani 1 1 d . . . . .
C1 C 0.8742(4) 1.1759(7) 0.7405(11) 0.052(2) Uani 1 1 d . . . . .
C2 C 0.8257(4) 1.1652(8) 0.7890(13) 0.068(3) Uani 1 1 d . . . . .
H2 H 0.811886 1.102338 0.800925 0.081 Uiso 1 1 calc R U . . .
C3 C 0.7992(4) 1.2490(9) 0.8183(13) 0.075(3) Uani 1 1 d . . . . .
H3 H 0.767140 1.242549 0.852255 0.090 Uiso 1 1 calc R U . . .
C4 C 0.8184(5) 1.3423(9) 0.7990(12) 0.070(3) Uani 1 1 d . . . . .
H4 H 0.798680 1.397909 0.815052 0.084 Uiso 1 1 calc R U . . .
C5 C 0.8657(4) 1.3548(8) 0.7570(12) 0.067(3) Uani 1 1 d . . . . .
H5 H 0.878928 1.418564 0.750297 0.081 Uiso 1 1 calc R U . . .
C6 C 0.8949(4) 1.2708(7) 0.7234(10) 0.051(2) Uani 1 1 d . . . . .
C7 C 0.9447(4) 1.2732(7) 0.6759(11) 0.054(2) Uani 1 1 d . . . . .
C8 C 0.9729(4) 1.3600(7) 0.6513(12) 0.065(3) Uani 1 1 d . . . . .
H8 H 0.958809 1.422293 0.666672 0.078 Uiso 1 1 calc R U . . .
C9 C 1.0204(4) 1.3538(10) 0.6052(14) 0.075(3) Uani 1 1 d . . . . .
H9 H 1.038437 1.411944 0.591892 0.090 Uiso 1 1 calc R U . . .
C10 C 1.0423(4) 1.2624(10) 0.5778(13) 0.076(3) Uani 1 1 d . . . . .
H10 H 1.074531 1.258991 0.544721 0.091 Uiso 1 1 calc R U . . .
C11 C 1.0161(4) 1.1787(8) 0.6000(13) 0.067(3) Uani 1 1 d . . . . .
H11 H 1.030780 1.117305 0.582403 0.081 Uiso 1 1 calc R U . . .
C12 C 0.9678(4) 1.1817(7) 0.6485(11) 0.056(2) Uani 1 1 d . . . . .
C13 C 0.6075(4) 0.2604(8) 0.3072(12) 0.059(2) Uani 1 1 d . . . . .
C14 C 0.6547(5) 0.2333(10) 0.4016(14) 0.079(3) Uani 1 1 d . . . . .
H14 H 0.676778 0.281912 0.453560 0.095 Uiso 1 1 calc R U . . .
C15 C 0.6676(5) 0.1357(10) 0.4158(15) 0.080(3) Uani 1 1 d . . . . .
H15 H 0.699449 0.118031 0.472606 0.095 Uiso 1 1 calc R U . . .
C16 C 0.6344(6) 0.0621(10) 0.3475(16) 0.090(4) Uani 1 1 d . . . . .
H16 H 0.643579 -0.004450 0.363696 0.108 Uiso 1 1 calc R U . . .
C17 C 0.5876(4) 0.0859(9) 0.2554(13) 0.073(3) Uani 1 1 d . . . . .
H17 H 0.565885 0.035921 0.206258 0.088 Uiso 1 1 calc R U . . .
C18 C 0.5729(4) 0.1876(7) 0.2365(12) 0.055(2) Uani 1 1 d . . . . .
C19 C 0.5261(4) 0.2227(7) 0.1475(12) 0.057(2) Uani 1 1 d . . . . .
C20 C 0.4859(4) 0.1618(8) 0.0752(13) 0.068(3) Uani 1 1 d . . . . .
H20 H 0.488677 0.092911 0.084373 0.081 Uiso 1 1 calc R U . . .
C21 C 0.4421(5) 0.2045(11) -0.0097(14) 0.084(3) Uani 1 1 d . . . . .
H21 H 0.415825 0.163528 -0.059939 0.100 Uiso 1 1 calc R U . . .
C22 C 0.4363(5) 0.3068(11) -0.0216(15) 0.081(3) Uani 1 1 d . . . . .
H22 H 0.406504 0.333636 -0.080413 0.097 Uiso 1 1 calc R U . . .
C23 C 0.4735(4) 0.3677(9) 0.0511(13) 0.070(3) Uani 1 1 d . . . . .
H23 H 0.469776 0.436568 0.044130 0.084 Uiso 1 1 calc R U . . .
C24 C 0.5188(4) 0.3239(8) 0.1391(12) 0.059(2) Uani 1 1 d . . . . .
C25 C 0.7945(4) 0.7937(7) 0.5266(12) 0.054(2) Uani 1 1 d . . . . .
C26 C 0.8070(3) 0.6960(7) 0.5585(12) 0.054(2) Uani 1 1 d . . . . .
C27 C 0.7724(4) 0.6194(7) 0.5116(12) 0.056(2) Uani 1 1 d . . . . .
C28 C 0.7239(4) 0.6384(7) 0.4305(11) 0.052(2) Uani 1 1 d . . . . .
C29 C 0.7119(4) 0.7344(7) 0.3945(12) 0.057(2) Uani 1 1 d . . . . .
C30 C 0.7461(4) 0.8115(7) 0.4432(12) 0.059(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C25 2.079(9) . ?
I2 C28 2.091(9) . ?
F1 C26 1.341(10) . ?
F2 C27 1.345(10) . ?
F3 C29 1.358(11) . ?
F4 C30 1.348(10) . ?
N1 N2 1.298(11) . ?
N1 C1 1.383(11) . ?
N2 C12 1.384(12) . ?
N3 N4 1.279(11) . ?
N3 C13 1.375(12) . ?
N4 C24 1.392(12) . ?
C1 C6 1.402(12) . ?
C1 C2 1.403(13) . ?
C2 C3 1.363(14) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.355(14) . ?
C4 H4 0.9300 . ?
C5 C6 1.413(13) . ?
C5 H5 0.9300 . ?
C6 C7 1.425(13) . ?
C7 C12 1.401(13) . ?
C7 C8 1.414(13) . ?
C8 C9 1.363(15) . ?
C8 H8 0.9300 . ?
C9 C10 1.387(15) . ?
C9 H9 0.9300 . ?
C10 C11 1.345(14) . ?
C10 H10 0.9300 . ?
C11 C12 1.391(14) . ?
C11 H11 0.9300 . ?
C13 C18 1.399(13) . ?
C13 C14 1.411(14) . ?
C14 C15 1.355(16) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(18) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(16) . ?
C16 H16 0.9300 . ?
C17 C18 1.422(14) . ?
C17 H17 0.9300 . ?
C18 C19 1.418(13) . ?
C19 C24 1.372(13) . ?
C19 C20 1.401(13) . ?
C20 C21 1.380(15) . ?
C20 H20 0.9300 . ?
C21 C22 1.383(16) . ?
C21 H21 0.9300 . ?
C22 C23 1.345(15) . ?
C22 H22 0.9300 . ?
C23 C24 1.426(14) . ?
C23 H23 0.9300 . ?
C25 C26 1.367(12) . ?
C25 C30 1.380(13) . ?
C26 C27 1.396(13) . ?
C27 C28 1.380(13) . ?
C28 C29 1.347(12) . ?
C29 C30 1.397(13) . ?

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
N2 N1 C1 121.2(8) . . ?
N1 N2 C12 118.9(8) . . ?
N4 N3 C13 122.0(9) . . ?
N3 N4 C24 118.3(8) . . ?
N1 C1 C6 123.2(9) . . ?
N1 C1 C2 116.4(9) . . ?
C6 C1 C2 120.5(9) . . ?
C3 C2 C1 118.5(10) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 121.8(11) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 120.9(10) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.9(10) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 118.3(9) . . ?
C1 C6 C7 115.8(8) . . ?
C5 C6 C7 125.8(9) . . ?
C12 C7 C8 116.8(9) . . ?
C12 C7 C6 117.5(9) . . ?
C8 C7 C6 125.7(9) . . ?
C9 C8 C7 120.9(10) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 121.2(11) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 118.9(11) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C12 121.7(11) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
N2 C12 C11 116.2(9) . . ?
N2 C12 C7 123.3(9) . . ?
C11 C12 C7 120.4(9) . . ?
N3 C13 C18 122.2(10) . . ?
N3 C13 C14 117.1(10) . . ?
C18 C13 C14 120.7(10) . . ?
C15 C14 C13 119.4(12) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 121.2(12) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C17 120.9(12) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C18 119.3(11) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C13 C18 C19 116.2(9) . . ?
C13 C18 C17 118.3(10) . . ?
C19 C18 C17 125.4(9) . . ?
C24 C19 C20 117.6(10) . . ?
C24 C19 C18 117.4(9) . . ?
C20 C19 C18 124.9(10) . . ?
C21 C20 C19 119.8(10) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 121.4(11) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C23 C22 C21 120.5(12) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 118.2(11) . . ?
C22 C23 H23 120.9 . . ?
C24 C23 H23 120.9 . . ?
C19 C24 N4 123.7(9) . . ?
C19 C24 C23 122.4(10) . . ?
N4 C24 C23 113.9(10) . . ?
C26 C25 C30 116.0(8) . . ?
C26 C25 I1 122.9(7) . . ?
C30 C25 I1 121.0(7) . . ?
F1 C26 C25 120.5(8) . . ?
F1 C26 C27 117.9(8) . . ?
C25 C26 C27 121.5(9) . . ?
F2 C27 C28 120.6(9) . . ?
F2 C27 C26 117.5(9) . . ?
C28 C27 C26 121.8(9) . . ?
C29 C28 C27 116.7(9) . . ?
C29 C28 I2 122.5(7) . . ?
C27 C28 I2 120.8(7) . . ?
C28 C29 F3 121.4(9) . . ?
C28 C29 C30 121.8(9) . . ?
F3 C29 C30 116.8(9) . . ?
F4 C30 C25 119.6(8) . . ?
F4 C30 C29 118.3(9) . . ?
C25 C30 C29 122.0(9) . . ?

_refine_diff_density_max         0.603
_refine_diff_density_min         -1.098
_refine_diff_density_rms         0.143


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 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_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1880030'
_audit_update_record             
;
2018-11-20 deposited with the CCDC.
2019-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
'Biphenyl Fluorene + 1,4-Diiodotetrafluorobenzene'
_chemical_name_common            
'Biphenyl Fluorene + 1,4-Diiodotetrafluorobenzene'
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H18 F4 I2'
_chemical_formula_sum            'C32 H18 F4 I2'
_chemical_formula_weight         732.26

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.3655(4)
_cell_length_b                   11.0244(4)
_cell_length_c                   13.4310(5)
_cell_angle_alpha                89.844(2)
_cell_angle_beta                 74.129(2)
_cell_angle_gamma                73.241(2)
_cell_volume                     1272.85(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9887
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      30.18

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.911
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.521
_shelx_estimated_absorpt_T_min   0.518
_shelx_estimated_absorpt_T_max   0.787
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.3584
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22991
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.936
_diffrn_reflns_theta_max         28.699
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6526
_reflns_number_gt                6117
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0309P)²+2.8469P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6526
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0820
_refine_ls_wR_factor_gt          0.0804
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.86237(2) 0.32540(2) 0.48339(2) 0.01708(7) Uani 1 1 d . . . . .
I2 I -0.14784(2) -0.25295(2) -0.00947(2) 0.01447(6) Uani 1 1 d . . . . .
F1 F 0.6893(2) 0.11487(18) 0.54852(16) 0.0199(4) Uani 1 1 d . . . . .
F2 F 1.2055(2) 0.13473(18) 0.44182(15) 0.0198(4) Uani 1 1 d . . . . .
F3 F 0.1991(2) -0.23875(16) -0.04768(15) 0.0152(4) Uani 1 1 d . . . . .
F4 F -0.3114(2) 0.04285(17) 0.04401(15) 0.0150(4) Uani 1 1 d . . . . .
C1 C 0.1881(4) 0.4377(3) 0.2757(3) 0.0172(6) Uani 1 1 d . . . . .
H1 H 0.121(6) 0.447(4) 0.343(4) 0.031(12) Uiso 1 1 d . . . . .
C2 C 0.3221(4) 0.3353(3) 0.2406(4) 0.0272(8) Uani 1 1 d . . . . .
H2 H 0.354(6) 0.272(5) 0.293(4) 0.034(12) Uiso 1 1 d . . . . .
C3 C 0.4126(4) 0.3244(3) 0.1396(4) 0.0276(9) Uani 1 1 d . . . . .
H3 H 0.493(7) 0.255(6) 0.118(5) 0.061(18) Uiso 1 1 d . . . . .
C4 C 0.3691(4) 0.4146(3) 0.0724(3) 0.0252(8) Uani 1 1 d . . . . .
H4 H 0.418(6) 0.410(5) 0.014(4) 0.031(13) Uiso 1 1 d . . . . .
C5 C 0.2357(4) 0.5172(3) 0.1072(3) 0.0168(6) Uani 1 1 d . . . . .
H5 H 0.202(4) 0.582(4) 0.064(3) 0.010(9) Uiso 1 1 d . . . . .
C6 C 0.1461(3) 0.5310(3) 0.2104(2) 0.0120(6) Uani 1 1 d . . . . .
C7 C -0.1770(4) 0.5287(3) 0.2205(3) 0.0135(6) Uani 1 1 d . . . . .
H7 H -0.100(5) 0.500(4) 0.152(3) 0.016(9) Uiso 1 1 d . . . . .
C8 C -0.3129(4) 0.4947(3) 0.2511(3) 0.0168(6) Uani 1 1 d . . . . .
H8 H -0.339(5) 0.445(4) 0.203(3) 0.020(10) Uiso 1 1 d . . . . .
C9 C -0.4145(4) 0.5370(3) 0.3493(3) 0.0193(7) Uani 1 1 d . . . . .
H9 H -0.501(5) 0.512(4) 0.371(3) 0.023(11) Uiso 1 1 d . . . . .
C10 C -0.3799(4) 0.6106(3) 0.4168(3) 0.0184(6) Uani 1 1 d . . . . .
H10 H -0.451(5) 0.634(4) 0.486(3) 0.022(10) Uiso 1 1 d . . . . .
C11 C -0.2431(4) 0.6449(3) 0.3862(2) 0.0148(6) Uani 1 1 d . . . . .
H11 H -0.215(5) 0.690(4) 0.429(4) 0.025(11) Uiso 1 1 d . . . . .
C12 C -0.1413(3) 0.6064(3) 0.2864(2) 0.0110(5) Uani 1 1 d . . . . .
C13 C 0.0051(3) 0.6423(3) 0.2507(2) 0.0097(5) Uani 1 1 d . . . . .
C14 C 0.0138(3) 0.7626(3) 0.2522(2) 0.0103(5) Uani 1 1 d . . . . .
C15 C -0.1147(3) 0.8845(3) 0.2717(2) 0.0093(5) Uani 1 1 d . . . . .
C16 C -0.2762(4) 0.9126(3) 0.2972(2) 0.0139(6) Uani 1 1 d . . . . .
H16 H -0.335(5) 0.847(4) 0.314(3) 0.018(10) Uiso 1 1 d . . . . .
C17 C -0.3679(4) 1.0385(3) 0.3103(3) 0.0156(6) Uani 1 1 d . . . . .
H17 H -0.483(6) 1.051(4) 0.329(4) 0.033(12) Uiso 1 1 d . . . . .
C18 C -0.3010(4) 1.1380(3) 0.2953(2) 0.0155(6) Uani 1 1 d . . . . .
H18 H -0.362(4) 1.216(4) 0.303(3) 0.006(8) Uiso 1 1 d . . . . .
C19 C -0.1408(4) 1.1118(3) 0.2672(2) 0.0142(6) Uani 1 1 d . . . . .
H19 H -0.087(5) 1.177(4) 0.253(3) 0.016(9) Uiso 1 1 d . . . . .
C20 C -0.0499(3) 0.9863(3) 0.2566(2) 0.0103(5) Uani 1 1 d . . . . .
C21 C 0.1196(3) 0.9346(3) 0.2298(2) 0.0107(5) Uani 1 1 d . . . . .
C22 C 0.2317(4) 0.9974(3) 0.2103(2) 0.0139(6) Uani 1 1 d . . . . .
H22 H 0.204(4) 1.087(4) 0.211(3) 0.012(9) Uiso 1 1 d . . . . .
C23 C 0.3863(4) 0.9268(3) 0.1907(2) 0.0173(6) Uani 1 1 d . . . . .
H23 H 0.466(5) 0.965(4) 0.179(3) 0.016(9) Uiso 1 1 d . . . . .
C24 C 0.4267(4) 0.7954(3) 0.1953(3) 0.0163(6) Uani 1 1 d . . . . .
H24 H 0.532(5) 0.742(4) 0.184(3) 0.014(9) Uiso 1 1 d . . . . .
C25 C 0.3137(4) 0.7319(3) 0.2151(2) 0.0141(6) Uani 1 1 d . . . . .
H25 H 0.346(4) 0.640(3) 0.223(3) 0.001(7) Uiso 1 1 d . . . . .
C26 C 0.1591(3) 0.8009(3) 0.2292(2) 0.0107(5) Uani 1 1 d . . . . .
C27 C 0.9438(4) 0.1319(3) 0.4955(2) 0.0133(6) Uani 1 1 d . . . . .
C28 C 0.8432(4) 0.0596(3) 0.5245(2) 0.0142(6) Uani 1 1 d . . . . .
C29 C 1.1018(4) 0.0696(3) 0.4716(2) 0.0140(6) Uani 1 1 d . . . . .
C30 C -0.0588(3) -0.1029(3) -0.0011(2) 0.0100(5) Uani 1 1 d . . . . .
C31 C 0.0984(3) -0.1212(3) -0.0234(2) 0.0104(5) Uani 1 1 d . . . . .
C32 C -0.1575(3) 0.0201(3) 0.0220(2) 0.0105(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C27 2.071(3) . ?
I2 C30 2.072(3) . ?
F1 C28 1.339(4) . ?
F2 C29 1.344(4) . ?
F3 C31 1.343(3) . ?
F4 C32 1.337(3) . ?
C1 C6 1.390(5) . ?
C1 C2 1.390(5) . ?
C1 H1 0.93(5) . ?
C2 C3 1.373(6) . ?
C2 H2 1.03(5) . ?
C3 C4 1.389(6) . ?
C3 H3 0.89(6) . ?
C4 C5 1.388(5) . ?
C4 H4 0.79(5) . ?
C5 C6 1.393(4) . ?
C5 H5 0.96(4) . ?
C6 C13 1.490(4) . ?
C7 C8 1.385(4) . ?
C7 C12 1.400(4) . ?
C7 H7 0.99(4) . ?
C8 C9 1.386(5) . ?
C8 H8 0.97(4) . ?
C9 C10 1.379(5) . ?
C9 H9 0.90(5) . ?
C10 C11 1.394(5) . ?
C10 H10 0.96(4) . ?
C11 C12 1.399(4) . ?
C11 H11 0.90(5) . ?
C12 C13 1.489(4) . ?
C13 C14 1.353(4) . ?
C14 C15 1.490(4) . ?
C14 C26 1.492(4) . ?
C15 C16 1.396(4) . ?
C15 C20 1.411(4) . ?
C16 C17 1.387(4) . ?
C16 H16 1.01(4) . ?
C17 C18 1.401(5) . ?
C17 H17 1.00(5) . ?
C18 C19 1.385(5) . ?
C18 H18 0.87(4) . ?
C19 C20 1.384(4) . ?
C19 H19 0.98(4) . ?
C20 C21 1.463(4) . ?
C21 C22 1.384(4) . ?
C21 C26 1.412(4) . ?
C22 C23 1.383(5) . ?
C22 H22 0.94(4) . ?
C23 C24 1.394(5) . ?
C23 H23 0.94(4) . ?
C24 C25 1.397(4) . ?
C24 H24 0.96(4) . ?
C25 C26 1.388(4) . ?
C25 H25 0.98(3) . ?
C27 C28 1.380(4) . ?
C27 C29 1.385(4) . ?
C28 C29 1.374(4) 2_756 ?
C30 C31 1.374(4) . ?
C30 C32 1.382(4) . ?
C31 C32 1.382(4) 2 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.8(3) . . ?
C6 C1 H1 117(3) . . ?
C2 C1 H1 122(3) . . ?
C3 C2 C1 119.8(4) . . ?
C3 C2 H2 121(3) . . ?
C1 C2 H2 119(3) . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3 118(4) . . ?
C4 C3 H3 122(4) . . ?
C5 C4 C3 120.4(4) . . ?
C5 C4 H4 117(4) . . ?
C3 C4 H4 122(4) . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 H5 123(2) . . ?
C6 C5 H5 117(2) . . ?
C1 C6 C5 119.1(3) . . ?
C1 C6 C13 119.9(3) . . ?
C5 C6 C13 121.0(3) . . ?
C8 C7 C12 121.1(3) . . ?
C8 C7 H7 123(2) . . ?
C12 C7 H7 116(2) . . ?
C7 C8 C9 119.5(3) . . ?
C7 C8 H8 120(3) . . ?
C9 C8 H8 120(3) . . ?
C10 C9 C8 120.5(3) . . ?
C10 C9 H9 119(3) . . ?
C8 C9 H9 120(3) . . ?
C9 C10 C11 120.2(3) . . ?
C9 C10 H10 118(3) . . ?
C11 C10 H10 122(3) . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11 123(3) . . ?
C12 C11 H11 117(3) . . ?
C11 C12 C7 118.4(3) . . ?
C11 C12 C13 121.8(3) . . ?
C7 C12 C13 119.8(3) . . ?
C14 C13 C12 125.0(3) . . ?
C14 C13 C6 121.8(3) . . ?
C12 C13 C6 113.2(2) . . ?
C13 C14 C15 128.8(3) . . ?
C13 C14 C26 126.3(3) . . ?
C15 C14 C26 104.9(2) . . ?
C16 C15 C20 118.3(3) . . ?
C16 C15 C14 132.8(3) . . ?
C20 C15 C14 108.9(2) . . ?
C17 C16 C15 119.5(3) . . ?
C17 C16 H16 116(2) . . ?
C15 C16 H16 125(2) . . ?
C16 C17 C18 121.2(3) . . ?
C16 C17 H17 115(3) . . ?
C18 C17 H17 124(3) . . ?
C19 C18 C17 120.1(3) . . ?
C19 C18 H18 122(2) . . ?
C17 C18 H18 118(2) . . ?
C20 C19 C18 118.6(3) . . ?
C20 C19 H19 117(2) . . ?
C18 C19 H19 124(2) . . ?
C19 C20 C15 122.3(3) . . ?
C19 C20 C21 129.0(3) . . ?
C15 C20 C21 108.7(2) . . ?
C22 C21 C26 121.8(3) . . ?
C22 C21 C20 129.7(3) . . ?
C26 C21 C20 108.5(2) . . ?
C23 C22 C21 118.9(3) . . ?
C23 C22 H22 120(2) . . ?
C21 C22 H22 121(2) . . ?
C22 C23 C24 120.1(3) . . ?
C22 C23 H23 122(2) . . ?
C24 C23 H23 118(2) . . ?
C23 C24 C25 121.0(3) . . ?
C23 C24 H24 123(2) . . ?
C25 C24 H24 116(2) . . ?
C26 C25 C24 119.4(3) . . ?
C26 C25 H25 122(2) . . ?
C24 C25 H25 118(2) . . ?
C25 C26 C21 118.7(3) . . ?
C25 C26 C14 132.3(3) . . ?
C21 C26 C14 108.9(3) . . ?
C28 C27 C29 117.6(3) . . ?
C28 C27 I1 121.3(2) . . ?
C29 C27 I1 121.1(2) . . ?
F1 C28 C29 118.8(3) . 2_756 ?
F1 C28 C27 120.1(3) . . ?
C29 C28 C27 121.0(3) 2_756 . ?
F2 C29 C28 118.3(3) . 2_756 ?
F2 C29 C27 120.3(3) . . ?
C28 C29 C27 121.4(3) 2_756 . ?
C31 C30 C32 118.2(3) . . ?
C31 C30 I2 121.6(2) . . ?
C32 C30 I2 120.1(2) . . ?
F3 C31 C30 120.5(3) . . ?
F3 C31 C32 118.2(3) . 2 ?
C30 C31 C32 121.3(3) . 2 ?
F4 C32 C31 119.1(3) . 2 ?
F4 C32 C30 120.5(3) . . ?
C31 C32 C30 120.5(3) 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
C6 C1 C2 C3 -1.4(5) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C3 C4 C5 1.2(5) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
C2 C1 C6 C5 3.4(5) . . . . ?
C2 C1 C6 C13 -177.9(3) . . . . ?
C4 C5 C6 C1 -3.1(4) . . . . ?
C4 C5 C6 C13 178.1(3) . . . . ?
C12 C7 C8 C9 -0.7(5) . . . . ?
C7 C8 C9 C10 -1.1(5) . . . . ?
C8 C9 C10 C11 1.0(5) . . . . ?
C9 C10 C11 C12 0.9(5) . . . . ?
C10 C11 C12 C7 -2.7(5) . . . . ?
C10 C11 C12 C13 179.4(3) . . . . ?
C8 C7 C12 C11 2.6(5) . . . . ?
C8 C7 C12 C13 -179.4(3) . . . . ?
C11 C12 C13 C14 -54.9(4) . . . . ?
C7 C12 C13 C14 127.2(3) . . . . ?
C11 C12 C13 C6 125.8(3) . . . . ?
C7 C12 C13 C6 -52.1(4) . . . . ?
C1 C6 C13 C14 118.9(3) . . . . ?
C5 C6 C13 C14 -62.4(4) . . . . ?
C1 C6 C13 C12 -61.8(4) . . . . ?
C5 C6 C13 C12 116.9(3) . . . . ?
C12 C13 C14 C15 -11.1(5) . . . . ?
C6 C13 C14 C15 168.2(3) . . . . ?
C12 C13 C14 C26 172.1(3) . . . . ?
C6 C13 C14 C26 -8.7(5) . . . . ?
C13 C14 C15 C16 2.9(5) . . . . ?
C26 C14 C15 C16 -179.7(3) . . . . ?
C13 C14 C15 C20 -174.9(3) . . . . ?
C26 C14 C15 C20 2.5(3) . . . . ?
C20 C15 C16 C17 -2.1(4) . . . . ?
C14 C15 C16 C17 -179.7(3) . . . . ?
C15 C16 C17 C18 2.0(5) . . . . ?
C16 C17 C18 C19 -0.2(5) . . . . ?
C17 C18 C19 C20 -1.3(5) . . . . ?
C18 C19 C20 C15 1.2(4) . . . . ?
C18 C19 C20 C21 -178.8(3) . . . . ?
C16 C15 C20 C19 0.6(4) . . . . ?
C14 C15 C20 C19 178.7(3) . . . . ?
C16 C15 C20 C21 -179.4(3) . . . . ?
C14 C15 C20 C21 -1.3(3) . . . . ?
C19 C20 C21 C22 1.5(5) . . . . ?
C15 C20 C21 C22 -178.5(3) . . . . ?
C19 C20 C21 C26 179.5(3) . . . . ?
C15 C20 C21 C26 -0.5(3) . . . . ?
C26 C21 C22 C23 -0.6(4) . . . . ?
C20 C21 C22 C23 177.1(3) . . . . ?
C21 C22 C23 C24 -2.9(5) . . . . ?
C22 C23 C24 C25 2.9(5) . . . . ?
C23 C24 C25 C26 0.7(5) . . . . ?
C24 C25 C26 C21 -4.1(4) . . . . ?
C24 C25 C26 C14 -179.2(3) . . . . ?
C22 C21 C26 C25 4.1(4) . . . . ?
C20 C21 C26 C25 -174.1(3) . . . . ?
C22 C21 C26 C14 -179.7(3) . . . . ?
C20 C21 C26 C14 2.1(3) . . . . ?
C13 C14 C26 C25 -9.9(5) . . . . ?
C15 C14 C26 C25 172.7(3) . . . . ?
C13 C14 C26 C21 174.7(3) . . . . ?
C15 C14 C26 C21 -2.8(3) . . . . ?
C29 C27 C28 F1 179.9(3) . . . . ?
I1 C27 C28 F1 -2.1(4) . . . . ?
C29 C27 C28 C29 -0.6(5) . . . 2_756 ?
I1 C27 C28 C29 177.4(2) . . . 2_756 ?
C28 C27 C29 F2 179.3(3) . . . . ?
I1 C27 C29 F2 1.3(4) . . . . ?
C28 C27 C29 C28 0.6(5) . . . 2_756 ?
I1 C27 C29 C28 -177.4(2) . . . 2_756 ?
C32 C30 C31 F3 -179.1(3) . . . . ?
I2 C30 C31 F3 -2.5(4) . . . . ?
C32 C30 C31 C32 0.6(5) . . . 2 ?
I2 C30 C31 C32 177.1(2) . . . 2 ?
C31 C30 C32 F4 179.8(3) . . . . ?
I2 C30 C32 F4 3.2(4) . . . . ?
C31 C30 C32 C31 -0.6(5) . . . 2 ?
I2 C30 C32 C31 -177.2(2) . . . 2 ?

_refine_diff_density_max         1.102
_refine_diff_density_min         -2.175
_refine_diff_density_rms         0.161


_exptl_crystal_preparation       Luminescent
