# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_psu-860(aggr-49)-4
_audit_block_doi                 10.5517/ccdc.csd.cc23nvxk
_database_code_depnum_ccdc_archive 'CCDC 1956469'
loop_
_audit_author_name
_audit_author_address
'Vladimir Zhulanov'
;Perm State University
Russia
;
_audit_update_record             
;
2019-09-28 deposited with the CCDC.	2019-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
2,7-bis(4-fluorophenyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H12 F2 N2 O4'
_chemical_formula_sum            'C26 H12 F2 N2 O4'
_chemical_formula_weight         454.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.538(5)
_cell_length_b                   8.3933(15)
_cell_length_c                   7.2050(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.82(3)
_cell_angle_gamma                90.00
_cell_volume                     978.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1388
_cell_measurement_theta_min      2.5100
_cell_measurement_theta_max      27.9720

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.56244
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5219
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         29.70
_reflns_number_total             2368
_reflns_number_gt                1539
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1009P)²+0.0986P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2368
_refine_ls_number_parameters     154
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1963
_refine_ls_wR_factor_gt          0.1658
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.098
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.00313(10) 0.5853(3) -0.2617(3) 0.1020(7) Uani 1 1 d . . .
C4 C 0.46083(12) 0.5105(2) 0.4419(3) 0.0378(5) Uani 1 1 d . . .
N1 N 0.30421(11) 0.54509(19) 0.2052(3) 0.0441(5) Uani 1 1 d . . .
C3 C 0.38962(12) 0.4647(2) 0.5077(3) 0.0402(5) Uani 1 1 d . . .
C5 C 0.45404(13) 0.5780(2) 0.2607(3) 0.0398(5) Uani 1 1 d . . .
C2 C 0.30739(13) 0.4848(2) 0.3859(3) 0.0445(5) Uani 1 1 d . . .
O1 O 0.36320(10) 0.6581(2) -0.0185(2) 0.0575(5) Uani 1 1 d . . .
C7 C 0.39813(14) 0.4004(2) 0.6859(3) 0.0457(5) Uani 1 1 d . . .
H7 H 0.3514 0.3705 0.7304 0.055 Uiso 1 1 calc R . .
C1 C 0.37196(13) 0.5995(2) 0.1366(3) 0.0425(5) Uani 1 1 d . . .
O2 O 0.24477(10) 0.44766(19) 0.4369(2) 0.0603(5) Uani 1 1 d . . .
C6 C 0.52407(14) 0.6205(2) 0.1997(3) 0.0454(5) Uani 1 1 d . . .
H6 H 0.5195 0.6641 0.0793 0.054 Uiso 1 1 calc R . .
C8 C 0.22436(12) 0.55742(19) 0.0826(3) 0.0471(6) Uani 1 1 d D . .
C9 C 0.18219(12) 0.7009(2) 0.0671(3) 0.0537(6) Uani 1 1 d D . .
H9 H 0.2057 0.7898 0.1341 0.064 Uiso 1 1 calc R . .
C11 C 0.07178(14) 0.5763(3) -0.1476(4) 0.0686(7) Uani 1 1 d D . .
C10 C 0.10444(13) 0.7107(3) -0.0497(4) 0.0669(7) Uani 1 1 d D . .
H10 H 0.0749 0.8057 -0.0616 0.080 Uiso 1 1 calc R . .
C13 C 0.19067(14) 0.4244(2) -0.0176(4) 0.0688(8) Uani 1 1 d D . .
H13 H 0.2199 0.3290 -0.0055 0.083 Uiso 1 1 calc R . .
C12 C 0.11354(14) 0.4329(3) -0.1358(4) 0.0795(9) Uani 1 1 d D . .
H12 H 0.0905 0.3448 -0.2052 0.095 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0567(11) 0.1230(17) 0.1113(14) 0.0098(12) -0.0177(10) 0.0033(9)
C4 0.0461(11) 0.0250(9) 0.0435(11) -0.0007(8) 0.0118(9) -0.0001(8)
N1 0.0442(10) 0.0347(9) 0.0513(10) 0.0015(8) 0.0050(8) -0.0012(7)
C3 0.0459(12) 0.0277(9) 0.0476(11) -0.0011(8) 0.0108(9) -0.0021(8)
C5 0.0491(12) 0.0288(9) 0.0410(11) -0.0005(8) 0.0081(9) 0.0001(8)
C2 0.0502(13) 0.0302(9) 0.0537(12) 0.0005(9) 0.0121(10) -0.0019(8)
O1 0.0592(10) 0.0605(11) 0.0507(9) 0.0134(8) 0.0060(7) 0.0000(7)
C7 0.0495(12) 0.0409(11) 0.0486(12) 0.0037(9) 0.0143(9) -0.0049(9)
C1 0.0514(13) 0.0318(9) 0.0441(11) 0.0006(9) 0.0096(9) -0.0004(8)
O2 0.0465(10) 0.0602(10) 0.0743(11) 0.0148(8) 0.0128(8) -0.0048(7)
C6 0.0568(13) 0.0377(11) 0.0428(11) 0.0066(9) 0.0127(10) -0.0024(9)
C8 0.0458(13) 0.0400(11) 0.0536(13) 0.0024(9) 0.0061(10) -0.0020(8)
C9 0.0624(15) 0.0424(12) 0.0554(13) 0.0009(10) 0.0099(11) 0.0066(10)
C11 0.0471(14) 0.0819(19) 0.0698(16) 0.0102(14) -0.0041(12) 0.0004(13)
C10 0.0636(16) 0.0628(16) 0.0722(16) 0.0102(14) 0.0093(13) 0.0201(13)
C13 0.0601(17) 0.0461(13) 0.092(2) -0.0082(13) -0.0039(14) 0.0007(11)
C12 0.0614(17) 0.0651(17) 0.100(2) -0.0112(16) -0.0117(16) -0.0115(13)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
F1 C11 1.341(3) . ?
C4 C4 1.403(4) 3_666 ?
C4 C5 1.406(3) . ?
C4 C3 1.410(3) . ?
N1 C2 1.387(3) . ?
N1 C1 1.391(3) . ?
N1 C8 1.434(3) . ?
C3 C7 1.373(3) . ?
C3 C2 1.470(3) . ?
C5 C6 1.368(3) . ?
C5 C1 1.476(3) . ?
C2 O2 1.209(3) . ?
O1 C1 1.202(2) . ?
C7 C6 1.390(3) 3_666 ?
C7 H7 0.9300 . ?
C6 C7 1.390(3) 3_666 ?
C6 H6 0.9300 . ?
C8 C13 1.3836(18) . ?
C8 C9 1.3845(18) . ?
C9 C10 1.3872(19) . ?
C9 H9 0.9300 . ?
C11 C10 1.3804(19) . ?
C11 C12 1.3814(19) . ?
C10 H10 0.9300 . ?
C13 C12 1.3829(19) . ?
C13 H13 0.9300 . ?
C12 H12 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
C4 C4 C5 119.6(2) 3_666 . ?
C4 C4 C3 119.9(2) 3_666 . ?
C5 C4 C3 120.57(19) . . ?
C2 N1 C1 125.07(18) . . ?
C2 N1 C8 117.21(17) . . ?
C1 N1 C8 117.68(17) . . ?
C7 C3 C4 119.3(2) . . ?
C7 C3 C2 120.58(19) . . ?
C4 C3 C2 120.15(19) . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 C1 120.48(18) . . ?
C4 C5 C1 120.05(18) . . ?
O2 C2 N1 120.6(2) . . ?
O2 C2 C3 122.3(2) . . ?
N1 C2 C3 117.06(18) . . ?
C3 C7 C6 120.6(2) . 3_666 ?
C3 C7 H7 119.7 . . ?
C6 C7 H7 119.7 3_666 . ?
O1 C1 N1 120.81(19) . . ?
O1 C1 C5 122.30(19) . . ?
N1 C1 C5 116.87(17) . . ?
C5 C6 C7 121.21(19) . 3_666 ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 3_666 . ?
C13 C8 C9 121.2(2) . . ?
C13 C8 N1 118.99(16) . . ?
C9 C8 N1 119.85(16) . . ?
C8 C9 C10 119.32(19) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
F1 C11 C10 118.9(2) . . ?
F1 C11 C12 118.3(2) . . ?
C10 C11 C12 122.8(2) . . ?
C11 C10 C9 118.6(2) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C12 C13 C8 120.1(2) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C11 C12 C13 118.0(2) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?

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
C4 C4 C3 C7 0.2(3) 3_666 . . . ?
C5 C4 C3 C7 -179.48(17) . . . . ?
C4 C4 C3 C2 -179.32(19) 3_666 . . . ?
C5 C4 C3 C2 1.0(3) . . . . ?
C4 C4 C5 C6 0.7(3) 3_666 . . . ?
C3 C4 C5 C6 -179.59(17) . . . . ?
C4 C4 C5 C1 179.49(19) 3_666 . . . ?
C3 C4 C5 C1 -0.8(3) . . . . ?
C1 N1 C2 O2 176.22(18) . . . . ?
C8 N1 C2 O2 -1.4(3) . . . . ?
C1 N1 C2 C3 -5.4(3) . . . . ?
C8 N1 C2 C3 176.98(15) . . . . ?
C7 C3 C2 O2 0.7(3) . . . . ?
C4 C3 C2 O2 -179.75(19) . . . . ?
C7 C3 C2 N1 -177.61(18) . . . . ?
C4 C3 C2 N1 1.9(3) . . . . ?
C4 C3 C7 C6 -0.3(3) . . . 3_666 ?
C2 C3 C7 C6 179.21(17) . . . 3_666 ?
C2 N1 C1 O1 -175.86(19) . . . . ?
C8 N1 C1 O1 1.7(3) . . . . ?
C2 N1 C1 C5 5.6(3) . . . . ?
C8 N1 C1 C5 -176.83(15) . . . . ?
C6 C5 C1 O1 -2.0(3) . . . . ?
C4 C5 C1 O1 179.20(19) . . . . ?
C6 C5 C1 N1 176.51(17) . . . . ?
C4 C5 C1 N1 -2.3(3) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . 3_666 ?
C1 C5 C6 C7 -179.39(18) . . . 3_666 ?
C2 N1 C8 C13 -83.2(3) . . . . ?
C1 N1 C8 C13 99.0(2) . . . . ?
C2 N1 C8 C9 96.5(2) . . . . ?
C1 N1 C8 C9 -81.3(3) . . . . ?
C13 C8 C9 C10 0.7(4) . . . . ?
N1 C8 C9 C10 -179.0(2) . . . . ?
F1 C11 C10 C9 -179.6(2) . . . . ?
C12 C11 C10 C9 -0.6(4) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C8 C13 C12 -0.1(4) . . . . ?
N1 C8 C13 C12 179.6(2) . . . . ?
F1 C11 C12 C13 -179.9(2) . . . . ?
C10 C11 C12 C13 1.2(5) . . . . ?
C8 C13 C12 C11 -0.8(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.853
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.053
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol or Acetic acid'
