# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_L-F
_database_code_depnum_ccdc_archive 'CCDC 1837781'
_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        '4?-p-fluorophenyl-2,2?:6?,2??-terpyridine '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 F N3'
_chemical_formula_weight         327.35

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'

_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                   3.8357(9)
_cell_length_b                   21.751(5)
_cell_length_c                   18.396(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.713(4)
_cell_angle_gamma                90
_cell_volume                     1533.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2489
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      27.52

_exptl_crystal_description       plates
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFARCTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7902
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.451
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3001
_reflns_number_gt                2519
_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 SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0432P)²+1.4395P] 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         3001
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0775
_refine_ls_wR_factor_ref         0.1546
_refine_ls_wR_factor_gt          0.1470
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_restrained_S_all      1.200
_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 1.2227(5) 0.55997(8) 0.42834(9) 0.0373(5) Uani 1 1 d . . . . .
N2 N 0.6746(5) 0.76394(10) 0.79472(11) 0.0221(5) Uani 1 1 d . . . . .
C9 C 0.8559(7) 0.75809(13) 0.67180(14) 0.0221(6) Uani 1 1 d . . . . .
C8 C 0.8684(6) 0.69468(12) 0.67427(14) 0.0212(6) Uani 1 1 d . . . . .
C10 C 0.7581(7) 0.79119(12) 0.73210(14) 0.0211(6) Uani 1 1 d . . . . .
C7 C 0.7845(7) 0.66611(13) 0.73897(14) 0.0213(6) Uani 1 1 d . . . . .
C11 C 0.7403(7) 0.85975(12) 0.72913(14) 0.0208(6) Uani 1 1 d . . . . .
C12 C 0.5975(7) 0.89364(13) 0.78439(15) 0.0238(6) Uani 1 1 d . . . . .
C6 C 0.6882(6) 0.70240(12) 0.79716(14) 0.0199(6) Uani 1 1 d . . . . .
C20 C 1.2067(7) 0.56727(13) 0.55565(15) 0.0243(6) Uani 1 1 d . . . . .
N1 N 0.6544(6) 0.61201(10) 0.87305(12) 0.0273(6) Uani 1 1 d . . . . .
C16 C 0.9632(6) 0.65814(12) 0.60926(14) 0.0200(6) Uani 1 1 d . . . . .
N3 N 0.8626(6) 0.88607(10) 0.66943(12) 0.0262(6) Uani 1 1 d . . . . .
C5 C 0.5920(7) 0.67242(12) 0.86680(14) 0.0211(6) Uani 1 1 d . . . . .
C17 C 0.8916(7) 0.68146(13) 0.53940(14) 0.0217(6) Uani 1 1 d . . . . .
C18 C 0.9759(7) 0.64860(13) 0.47805(14) 0.0239(6) Uani 1 1 d . . . . .
C14 C 0.7104(8) 0.98447(14) 0.71743(16) 0.0293(7) Uani 1 1 d . . . . .
C21 C 1.1220(7) 0.60072(12) 0.61620(15) 0.0218(6) Uani 1 1 d . . . . .
C4 C 0.4454(7) 0.70651(14) 0.92189(14) 0.0241(6) Uani 1 1 d . . . . .
C1 C 0.5747(8) 0.58470(14) 0.93543(16) 0.0312(7) Uani 1 1 d . . . . .
C13 C 0.5829(8) 0.95667(13) 0.77845(15) 0.0273(7) Uani 1 1 d . . . . .
C3 C 0.3680(8) 0.67729(14) 0.98570(15) 0.0282(7) Uani 1 1 d . . . . .
C15 C 0.8469(8) 0.94694(13) 0.66514(15) 0.0283(7) Uani 1 1 d . . . . .
C2 C 0.4342(8) 0.61526(14) 0.99295(16) 0.0291(7) Uani 1 1 d . . . . .
C19 C 1.1344(7) 0.59236(12) 0.48796(14) 0.0221(6) Uani 1 1 d . . . . .
H4 H 0.407(7) 0.7481(13) 0.9138(14) 0.019(7) Uiso 1 1 d . . . . .
H14 H 0.713(7) 1.0291(12) 0.7103(14) 0.017(7) Uiso 1 1 d . . . . .
H9 H 0.924(7) 0.7798(12) 0.6305(15) 0.019(7) Uiso 1 1 d . . . . .
H7 H 0.786(7) 0.6232(13) 0.7439(14) 0.020(7) Uiso 1 1 d . . . . .
H21 H 1.170(7) 0.5848(12) 0.6649(16) 0.024(7) Uiso 1 1 d . . . . .
H20 H 1.323(8) 0.5264(14) 0.5584(16) 0.031(8) Uiso 1 1 d . . . . .
H1 H 0.628(7) 0.5409(13) 0.9387(15) 0.024(7) Uiso 1 1 d . . . . .
H17 H 0.773(7) 0.7207(13) 0.5320(15) 0.025(7) Uiso 1 1 d . . . . .
H15 H 0.939(8) 0.9638(13) 0.6223(16) 0.029(8) Uiso 1 1 d . . . . .
H18 H 0.917(7) 0.6644(12) 0.4316(16) 0.026(8) Uiso 1 1 d . . . . .
H2 H 0.381(8) 0.5903(14) 1.0389(17) 0.039(9) Uiso 1 1 d . . . . .
H12 H 0.507(7) 0.8736(12) 0.8240(16) 0.022(7) Uiso 1 1 d . . . . .
H13 H 0.476(8) 0.9817(13) 0.8138(17) 0.030(8) Uiso 1 1 d . . . . .
H3 H 0.268(8) 0.7021(14) 1.0242(17) 0.038(9) Uiso 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
F1 C19 1.360(3) . ?
N2 C6 1.340(3) . ?
N2 C10 1.348(3) . ?
C9 C8 1.381(4) . ?
C9 C10 1.389(4) . ?
C9 H9 0.94(3) . ?
C8 C7 1.394(4) . ?
C8 C16 1.495(4) . ?
C10 C11 1.494(4) . ?
C7 C6 1.394(4) . ?
C7 H7 0.94(3) . ?
C11 N3 1.343(3) . ?
C11 C12 1.389(4) . ?
C12 C13 1.376(4) . ?
C12 H12 0.93(3) . ?
C6 C5 1.499(4) . ?
C20 C19 1.376(4) . ?
C20 C21 1.382(4) . ?
C20 H20 0.99(3) . ?
N1 C5 1.340(3) . ?
N1 C1 1.340(4) . ?
C16 C21 1.393(4) . ?
C16 C17 1.397(4) . ?
N3 C15 1.327(4) . ?
C5 C4 1.395(4) . ?
C17 C18 1.387(4) . ?
C17 H17 0.97(3) . ?
C18 C19 1.374(4) . ?
C18 H18 0.94(3) . ?
C14 C15 1.383(4) . ?
C14 C13 1.385(4) . ?
C14 H14 0.98(3) . ?
C21 H21 0.97(3) . ?
C4 C3 1.379(4) . ?
C4 H4 0.93(3) . ?
C1 C2 1.380(4) . ?
C1 H1 0.98(3) . ?
C13 H13 0.96(3) . ?
C3 C2 1.378(4) . ?
C3 H3 0.98(3) . ?
C15 H15 0.95(3) . ?
C2 H2 1.03(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
C6 N2 C10 117.2(2) . . ?
C8 C9 C10 120.1(3) . . ?
C8 C9 H9 121.1(16) . . ?
C10 C9 H9 118.7(16) . . ?
C9 C8 C7 117.7(2) . . ?
C9 C8 C16 120.9(2) . . ?
C7 C8 C16 121.4(2) . . ?
N2 C10 C9 122.6(3) . . ?
N2 C10 C11 117.3(2) . . ?
C9 C10 C11 120.1(2) . . ?
C8 C7 C6 118.9(3) . . ?
C8 C7 H7 121.7(17) . . ?
C6 C7 H7 119.4(17) . . ?
N3 C11 C12 122.5(2) . . ?
N3 C11 C10 116.0(2) . . ?
C12 C11 C10 121.5(2) . . ?
C13 C12 C11 119.1(3) . . ?
C13 C12 H12 120.9(17) . . ?
C11 C12 H12 120.0(17) . . ?
N2 C6 C7 123.4(2) . . ?
N2 C6 C5 116.9(2) . . ?
C7 C6 C5 119.7(2) . . ?
C19 C20 C21 118.4(3) . . ?
C19 C20 H20 118.1(17) . . ?
C21 C20 H20 123.5(17) . . ?
C5 N1 C1 117.5(2) . . ?
C21 C16 C17 118.4(2) . . ?
C21 C16 C8 121.7(2) . . ?
C17 C16 C8 119.9(2) . . ?
C15 N3 C11 117.2(2) . . ?
N1 C5 C4 122.4(2) . . ?
N1 C5 C6 116.7(2) . . ?
C4 C5 C6 120.9(2) . . ?
C18 C17 C16 121.2(3) . . ?
C18 C17 H17 117.6(16) . . ?
C16 C17 H17 121.1(16) . . ?
C19 C18 C17 118.0(3) . . ?
C19 C18 H18 122.1(17) . . ?
C17 C18 H18 119.9(17) . . ?
C15 C14 C13 117.8(3) . . ?
C15 C14 H14 119.0(16) . . ?
C13 C14 H14 123.2(16) . . ?
C20 C21 C16 121.1(3) . . ?
C20 C21 H21 121.0(16) . . ?
C16 C21 H21 117.9(16) . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 H4 123.2(17) . . ?
C5 C4 H4 117.9(17) . . ?
N1 C1 C2 123.8(3) . . ?
N1 C1 H1 115.5(17) . . ?
C2 C1 H1 120.7(17) . . ?
C12 C13 C14 119.0(3) . . ?
C12 C13 H13 122.0(18) . . ?
C14 C13 H13 118.9(18) . . ?
C2 C3 C4 119.2(3) . . ?
C2 C3 H3 122.9(18) . . ?
C4 C3 H3 117.9(18) . . ?
N3 C15 C14 124.4(3) . . ?
N3 C15 H15 114.6(17) . . ?
C14 C15 H15 121.0(17) . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 H2 123.5(17) . . ?
C1 C2 H2 118.2(17) . . ?
F1 C19 C18 118.7(2) . . ?
F1 C19 C20 118.5(2) . . ?
C18 C19 C20 122.8(2) . . ?

_refine_diff_density_max         0.306
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.060



