# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_ydkr2
_database_code_depnum_ccdc_archive 'CCDC 1436269'
_audit_update_record             
;
2015-11-11 deposited with the CCDC.
2015-12-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        B4PyMFB
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H25 F N4'
_chemical_formula_sum            'C38 H25 F N4'
_chemical_formula_weight         556.62

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           31
_space_group_name_H-M_alt        'P m n 21'
_space_group_name_Hall           'P 2ac -2'

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

_cell_length_a                   33.005(12)
_cell_length_b                   3.7442(13)
_cell_length_c                   10.782(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1332.4(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    93
_cell_measurement_reflns_used    3496
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      30.4

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             580
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            15232
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.987
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2817
_reflns_number_gt                2708
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.997

_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       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_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)+(0.0801P)²] 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_abs_structure_details 
;
 Flack x determined using 1230 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2817
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.5000 -0.4299(5) 0.48037(17) 0.0221(4) Uani 1 2 d S T P . .
N1 N 0.24349(5) 0.3932(5) 0.33124(18) 0.0194(4) Uani 1 1 d . . . . .
N2 N 0.38561(6) -0.0796(5) -0.46672(17) 0.0211(4) Uani 1 1 d . . . . .
C1 C 0.5000 -0.2840(8) 0.3648(3) 0.0170(6) Uani 1 2 d S T P . .
C2 C 0.46312(6) -0.2165(6) 0.3093(2) 0.0167(4) Uani 1 1 d . . . . .
H2 H 0.4385 -0.2690 0.3509 0.020 Uiso 1 1 calc R U . . .
C3 C 0.46301(6) -0.0691(5) 0.1903(2) 0.0151(4) Uani 1 1 d . . . . .
C4 C 0.5000 0.0075(8) 0.1326(3) 0.0160(6) Uani 1 2 d S T P . .
H4 H 0.5000 0.1137 0.0526 0.019 Uiso 1 2 calc R U P . .
C5 C 0.38954(6) 0.1060(6) 0.1883(2) 0.0156(4) Uani 1 1 d . . . . .
H5 H 0.3906 0.1297 0.2760 0.019 Uiso 1 1 calc R U . . .
C6 C 0.35292(6) 0.1713(6) 0.12567(19) 0.0158(5) Uani 1 1 d . . . . .
C7 C 0.35199(6) 0.1397(6) -0.0038(2) 0.0163(4) Uani 1 1 d . . . . .
H7 H 0.3275 0.1840 -0.0472 0.020 Uiso 1 1 calc R U . . .
C8 C 0.38670(7) 0.0439(6) -0.06952(19) 0.0153(5) Uani 1 1 d . . . . .
C9 C 0.42254(6) -0.0234(5) -0.0051(2) 0.0155(4) Uani 1 1 d . . . . .
H9 H 0.4462 -0.0911 -0.0496 0.019 Uiso 1 1 calc R U . . .
C10 C 0.42427(6) 0.0070(6) 0.12364(19) 0.0155(4) Uani 1 1 d . . . . .
C11 C 0.27531(6) 0.2272(6) 0.3822(2) 0.0197(5) Uani 1 1 d . . . . .
H11 H 0.2731 0.1523 0.4661 0.024 Uiso 1 1 calc R U . . .
C12 C 0.24807(7) 0.4951(6) 0.2125(2) 0.0188(5) Uani 1 1 d . . . . .
H12 H 0.2262 0.6172 0.1741 0.023 Uiso 1 1 calc R U . . .
C13 C 0.28271(6) 0.4336(6) 0.1423(2) 0.0175(5) Uani 1 1 d . . . . .
H13 H 0.2840 0.5103 0.0585 0.021 Uiso 1 1 calc R U . . .
C14 C 0.31552(6) 0.2583(6) 0.19632(19) 0.0161(4) Uani 1 1 d . . . . .
C15 C 0.31144(6) 0.1570(6) 0.3206(2) 0.0185(5) Uani 1 1 d . . . . .
H15 H 0.3331 0.0414 0.3624 0.022 Uiso 1 1 calc R U . . .
C16 C 0.38599(6) 0.0050(6) -0.20704(19) 0.0157(5) Uani 1 1 d . . . . .
C17 C 0.35264(6) -0.1411(6) -0.2682(2) 0.0180(5) Uani 1 1 d . . . . .
H17 H 0.3293 -0.2129 -0.2231 0.022 Uiso 1 1 calc R U . . .
C18 C 0.35419(6) -0.1796(6) -0.3961(2) 0.0196(5) Uani 1 1 d . . . . .
H18 H 0.3315 -0.2838 -0.4362 0.024 Uiso 1 1 calc R U . . .
C19 C 0.41732(7) 0.0653(6) -0.4070(2) 0.0202(5) Uani 1 1 d . . . . .
H19 H 0.4399 0.1411 -0.4547 0.024 Uiso 1 1 calc R U . . .
C20 C 0.41886(6) 0.1101(6) -0.2795(2) 0.0185(5) Uani 1 1 d . . . . .
H20 H 0.4422 0.2118 -0.2417 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
F1 C1 1.360(3) . ?
N1 C11 1.338(3) . ?
N1 C12 1.344(3) . ?
N2 C18 1.340(3) . ?
N2 C19 1.344(3) . ?
C1 C2 1.380(2) . ?
C1 C2 1.380(2) 3_655 ?
C2 C3 1.397(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.400(2) . ?
C3 C10 1.494(3) . ?
C4 C3 1.400(2) 3_655 ?
C4 H4 0.9500 . ?
C5 C10 1.392(3) . ?
C5 C6 1.406(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.401(3) . ?
C6 C14 1.486(3) . ?
C7 C8 1.394(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.395(3) . ?
C8 C16 1.490(3) . ?
C9 C10 1.394(3) . ?
C9 H9 0.9500 . ?
C11 C15 1.390(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.399(3) . ?
C15 H15 0.9500 . ?
C16 C20 1.393(3) . ?
C16 C17 1.395(3) . ?
C17 C18 1.387(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.386(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C12 115.74(18) . . ?
C18 N2 C19 116.3(2) . . ?
F1 C1 C2 118.11(13) . . ?
F1 C1 C2 118.11(13) . 3_655 ?
C2 C1 C2 123.8(3) . 3_655 ?
C1 C2 C3 118.27(19) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C2 C3 C4 119.1(2) . . ?
C2 C3 C10 121.31(18) . . ?
C4 C3 C10 119.6(2) . . ?
C3 C4 C3 121.4(3) . 3_655 ?
C3 C4 H4 119.3 . . ?
C3 C4 H4 119.3 3_655 . ?
C10 C5 C6 120.88(19) . . ?
C10 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 118.87(19) . . ?
C7 C6 C14 120.72(18) . . ?
C5 C6 C14 120.37(18) . . ?
C8 C7 C6 120.67(18) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 119.36(19) . . ?
C7 C8 C16 121.19(19) . . ?
C9 C8 C16 119.44(19) . . ?
C10 C9 C8 121.07(19) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C5 C10 C9 119.1(2) . . ?
C5 C10 C3 120.95(19) . . ?
C9 C10 C3 119.91(19) . . ?
N1 C11 C15 124.4(2) . . ?
N1 C11 H11 117.8 . . ?
C15 C11 H11 117.8 . . ?
N1 C12 C13 124.3(2) . . ?
N1 C12 H12 117.8 . . ?
C13 C12 H12 117.8 . . ?
C12 C13 C14 119.3(2) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C15 116.92(18) . . ?
C13 C14 C6 122.30(19) . . ?
C15 C14 C6 120.75(18) . . ?
C11 C15 C14 119.27(19) . . ?
C11 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C20 C16 C17 117.38(19) . . ?
C20 C16 C8 121.2(2) . . ?
C17 C16 C8 121.42(19) . . ?
C18 C17 C16 118.79(19) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
N2 C18 C17 124.4(2) . . ?
N2 C18 H18 117.8 . . ?
C17 C18 H18 117.8 . . ?
N2 C19 C20 123.6(2) . . ?
N2 C19 H19 118.2 . . ?
C20 C19 H19 118.2 . . ?
C19 C20 C16 119.6(2) . . ?
C19 C20 H20 120.2 . . ?
C16 C20 H20 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 C3 -179.6(2) . . . . ?
C2 C1 C2 C3 -0.5(4) 3_655 . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C1 C2 C3 C10 179.2(2) . . . . ?
C2 C3 C4 C3 1.7(4) . . . 3_655 ?
C10 C3 C4 C3 -178.14(18) . . . 3_655 ?
C10 C5 C6 C7 -0.8(3) . . . . ?
C10 C5 C6 C14 176.8(2) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C14 C6 C7 C8 -177.39(19) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
C6 C7 C8 C16 179.2(2) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?
C16 C8 C9 C10 -179.41(19) . . . . ?
C6 C5 C10 C9 0.7(3) . . . . ?
C6 C5 C10 C3 -178.85(19) . . . . ?
C8 C9 C10 C5 0.1(3) . . . . ?
C8 C9 C10 C3 179.60(19) . . . . ?
C2 C3 C10 C5 32.2(3) . . . . ?
C4 C3 C10 C5 -148.0(2) . . . . ?
C2 C3 C10 C9 -147.3(2) . . . . ?
C4 C3 C10 C9 32.5(3) . . . . ?
C12 N1 C11 C15 -0.2(3) . . . . ?
C11 N1 C12 C13 1.0(3) . . . . ?
N1 C12 C13 C14 -0.6(3) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C12 C13 C14 C6 177.6(2) . . . . ?
C7 C6 C14 C13 -23.5(3) . . . . ?
C5 C6 C14 C13 158.9(2) . . . . ?
C7 C6 C14 C15 154.7(2) . . . . ?
C5 C6 C14 C15 -22.9(3) . . . . ?
N1 C11 C15 C14 -1.1(4) . . . . ?
C13 C14 C15 C11 1.4(3) . . . . ?
C6 C14 C15 C11 -176.9(2) . . . . ?
C7 C8 C16 C20 142.9(2) . . . . ?
C9 C8 C16 C20 -38.3(3) . . . . ?
C7 C8 C16 C17 -37.7(3) . . . . ?
C9 C8 C16 C17 141.0(2) . . . . ?
C20 C16 C17 C18 1.1(3) . . . . ?
C8 C16 C17 C18 -178.2(2) . . . . ?
C19 N2 C18 C17 0.3(3) . . . . ?
C16 C17 C18 N2 -1.2(4) . . . . ?
C18 N2 C19 C20 0.7(3) . . . . ?
N2 C19 C20 C16 -0.7(4) . . . . ?
C17 C16 C20 C19 -0.3(3) . . . . ?
C8 C16 C20 C19 179.1(2) . . . . ?

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.077



