# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_gc45

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H19 F4 N'
_chemical_formula_sum            'C24 H19 F4 N'
_chemical_formula_weight         397.40

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'

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                   7.594(5)
_cell_length_b                   5.874(4)
_cell_length_c                   41.51(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.302(8)
_cell_angle_gamma                90.00
_cell_volume                     1846(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    886
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      20.17

_exptl_crystal_description       lamina
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   none

_exptl_special_details           
;

The crystals were always twinned and/or curved. The sample chosen was 
apparently the best for dimensions and quality of the diffraction. 
It was put on a very thin, rigid lamina obtained exploding a bubble 
of fused glass; the crystal was fixed on the lamina through a film 
of a highly dense perfluorurated compound; this technique assured a good
adhesion between glass and crystal and prevented the crystal curvature 
increasing in the course of freezing process.  
In spite of the long time of data collection (120"/frame) it was impossible 
to collect data at theta > 21 %o. 
Moreover, due to the very anisotropic form of the spot, probably due to 
the curvature of the crystal, a number of reflections were not integrated,
so that the data quality is very poor and the resolution is low.
Notwithstanding, the structure solution was easy and there is no question 
about the correctness of the structure.
The temperature was controlled by a Bruker KRYOFLEX low temperature device. 
;

_diffrn_ambient_temperature      103(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  'Bruker APEX-II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5727
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_av_sigmaI/netI    0.1010
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         20.81
_reflns_number_total             1814
_reflns_number_gt                1100
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    
;
SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., 
Giacovazzo, C., Polidori, G. & Spagna, R. (2003). 
J. Appl. Cryst. 36, 1103.)
;
_computing_structure_refinement  SHELXL_97

_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565)
Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., 
Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). 
J. Appl. Cryst. 39, 453-457
;
_computing_publication_material  SHELXL-97


_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 > 2sigma(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. 

Fluorine atoms and dimethylamino group were refined anisotropically.
We refined the others C atoms isotropically to have a sufficiently high
data/parameters ratio.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1036P)²+19.5133P] 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     SHELXL
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1814
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1646
_refine_ls_R_factor_gt           0.1134
_refine_ls_wR_factor_ref         0.2943
_refine_ls_wR_factor_gt          0.2673
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.2086(7) 0.7381(10) 1.06099(14) 0.0315(18) Uani 1 1 d . . .
F2 F 0.2875(7) 0.6470(11) 1.12305(14) 0.0359(19) Uani 1 1 d . . .
F3 F 0.5483(7) -0.0508(11) 1.09607(14) 0.0331(18) Uani 1 1 d . . .
F4 F 0.4711(7) 0.0344(10) 1.03354(14) 0.0292(18) Uani 1 1 d . . .
N1 N -0.3333(12) 0.8403(17) 0.7096(2) 0.037(3) Uani 1 1 d . . .
C1 C 0.2958(13) 0.5356(18) 1.0687(2) 0.022(3) Uiso 1 1 d . . .
C2 C 0.3338(14) 0.4950(19) 1.1006(2) 0.024(3) Uiso 1 1 d . . .
C3 C 0.4197(13) 0.2981(18) 1.1109(3) 0.023(3) Uiso 1 1 d . . .
H3 H 0.4489 0.2690 1.1332 0.027 Uiso 1 1 calc R . .
C4 C 0.4614(13) 0.1454(18) 1.0874(2) 0.021(3) Uiso 1 1 d . . .
C5 C 0.4229(13) 0.1905(18) 1.0555(2) 0.021(3) Uiso 1 1 d . . .
C6 C 0.3364(13) 0.3873(18) 1.0440(2) 0.021(3) Uiso 1 1 d . . .
C7 C 0.2969(13) 0.4201(19) 1.0097(2) 0.027(3) Uiso 1 1 d . . .
H7 H 0.3364 0.3037 0.9961 0.033 Uiso 1 1 calc R . .
C8 C 0.2102(14) 0.5967(19) 0.9946(2) 0.028(3) Uiso 1 1 d . . .
H8 H 0.1714 0.7162 1.0078 0.034 Uiso 1 1 calc R . .
C9 C 0.1713(13) 0.6182(18) 0.9593(2) 0.022(3) Uiso 1 1 d . . .
C10 C 0.2086(13) 0.4452(19) 0.9375(2) 0.023(3) Uiso 1 1 d . . .
H10 H 0.2644 0.3086 0.9451 0.028 Uiso 1 1 calc R . .
C11 C 0.1636(14) 0.4749(19) 0.9046(3) 0.029(3) Uiso 1 1 d . . .
H11 H 0.1909 0.3569 0.8902 0.035 Uiso 1 1 calc R . .
C12 C 0.0799(13) 0.6712(19) 0.8921(2) 0.025(3) Uiso 1 1 d . . .
C13 C 0.0472(13) 0.8439(19) 0.9141(2) 0.027(3) Uiso 1 1 d . . .
H13 H -0.0055 0.9823 0.9065 0.033 Uiso 1 1 calc R . .
C14 C 0.0910(13) 0.8152(19) 0.9471(2) 0.029(3) Uiso 1 1 d . . .
H14 H 0.0651 0.9338 0.9615 0.035 Uiso 1 1 calc R . .
C15 C 0.0296(15) 0.680(2) 0.8579(3) 0.036(3) Uiso 1 1 d . . .
H15 H 0.0724 0.5606 0.8451 0.043 Uiso 1 1 calc R . .
C16 C -0.0721(14) 0.840(2) 0.8420(3) 0.031(3) Uiso 1 1 d . . .
H16 H -0.1073 0.9652 0.8544 0.037 Uiso 1 1 calc R . .
C17 C -0.1335(14) 0.8410(19) 0.8078(3) 0.028(3) Uiso 1 1 d . . .
C18 C -0.0890(14) 0.670(2) 0.7859(3) 0.034(3) Uiso 1 1 d . . .
H18 H -0.0140 0.5492 0.7937 0.040 Uiso 1 1 calc R . .
C19 C -0.1494(14) 0.670(2) 0.7540(3) 0.031(3) Uiso 1 1 d . . .
H19 H -0.1139 0.5541 0.7399 0.037 Uiso 1 1 calc R . .
C20 C -0.2661(15) 0.847(2) 0.7419(3) 0.031(3) Uiso 1 1 d . . .
C21 C -0.3083(14) 1.0171(19) 0.7631(2) 0.028(3) Uiso 1 1 d . . .
H21 H -0.3829 1.1385 0.7555 0.034 Uiso 1 1 calc R . .
C22 C -0.2434(14) 1.013(2) 0.7953(3) 0.032(3) Uiso 1 1 d . . .
H22 H -0.2752 1.1328 0.8091 0.039 Uiso 1 1 calc R . .
C23 C -0.2810(15) 0.666(2) 0.6882(3) 0.039(3) Uani 1 1 d . . .
H23A H -0.1520 0.6659 0.6879 0.058 Uiso 1 1 calc R . .
H23B H -0.3344 0.6959 0.6663 0.058 Uiso 1 1 calc R . .
H23C H -0.3206 0.5178 0.6956 0.058 Uiso 1 1 calc R . .
C24 C -0.4526(15) 1.019(2) 0.6975(3) 0.043(4) Uani 1 1 d . . .
H24A H -0.5579 1.0190 0.7097 0.065 Uiso 1 1 calc R . .
H24B H -0.4872 0.9913 0.6746 0.065 Uiso 1 1 calc R . .
H24C H -0.3931 1.1665 0.6999 0.065 Uiso 1 1 calc R . .


_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 1.387(12) . ?
F2 C2 1.355(12) . ?
F3 C4 1.363(12) . ?
F4 C5 1.362(11) . ?
N1 C20 1.397(13) . ?
N1 C23 1.432(14) . ?
N1 C24 1.451(14) . ?
C1 C2 1.356(14) . ?
C1 C6 1.395(14) . ?
C2 C3 1.379(15) . ?
C3 C4 1.378(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.362(13) . ?
C5 C6 1.395(14) . ?
C6 C7 1.448(14) . ?
C7 C8 1.356(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.478(14) . ?
C8 H8 0.9500 . ?
C9 C14 1.387(15) . ?
C9 C10 1.405(14) . ?
C10 C11 1.391(14) . ?
C10 H10 0.9500 . ?
C11 C12 1.399(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.402(14) . ?
C12 C15 1.442(14) . ?
C13 C14 1.392(14) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.357(15) . ?
C15 H15 0.9500 . ?
C16 C17 1.459(15) . ?
C16 H16 0.9500 . ?
C17 C22 1.388(15) . ?
C17 C18 1.412(15) . ?
C18 C19 1.372(14) . ?
C18 H18 0.9500 . ?
C19 C20 1.429(15) . ?
C19 H19 0.9500 . ?
C20 C21 1.387(15) . ?
C21 C22 1.388(14) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
C20 N1 C23 121.1(9) . . ?
C20 N1 C24 119.2(10) . . ?
C23 N1 C24 119.7(10) . . ?
C2 C1 F1 116.0(9) . . ?
C2 C1 C6 124.4(10) . . ?
F1 C1 C6 119.6(9) . . ?
F2 C2 C1 120.6(10) . . ?
F2 C2 C3 118.8(9) . . ?
C1 C2 C3 120.6(10) . . ?
C4 C3 C2 117.1(10) . . ?
C4 C3 H3 121.4 . . ?
C2 C3 H3 121.4 . . ?
C5 C4 F3 119.0(9) . . ?
C5 C4 C3 121.2(10) . . ?
F3 C4 C3 119.8(9) . . ?
C4 C5 F4 118.2(9) . . ?
C4 C5 C6 123.6(10) . . ?
F4 C5 C6 118.2(9) . . ?
C1 C6 C5 113.1(10) . . ?
C1 C6 C7 126.7(10) . . ?
C5 C6 C7 120.2(9) . . ?
C8 C7 C6 127.9(10) . . ?
C8 C7 H7 116.1 . . ?
C6 C7 H7 116.1 . . ?
C7 C8 C9 125.3(10) . . ?
C7 C8 H8 117.4 . . ?
C9 C8 H8 117.4 . . ?
C14 C9 C10 118.1(10) . . ?
C14 C9 C8 119.0(10) . . ?
C10 C9 C8 122.9(10) . . ?
C11 C10 C9 119.7(10) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 122.7(10) . . ?
C10 C11 H11 118.7 . . ?
C12 C11 H11 118.7 . . ?
C11 C12 C13 116.8(10) . . ?
C11 C12 C15 118.4(10) . . ?
C13 C12 C15 124.8(10) . . ?
C14 C13 C12 120.9(11) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C9 C14 C13 121.8(10) . . ?
C9 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C16 C15 C12 127.1(11) . . ?
C16 C15 H15 116.5 . . ?
C12 C15 H15 116.5 . . ?
C15 C16 C17 127.3(11) . . ?
C15 C16 H16 116.4 . . ?
C17 C16 H16 116.4 . . ?
C22 C17 C18 116.4(10) . . ?
C22 C17 C16 120.4(10) . . ?
C18 C17 C16 123.1(11) . . ?
C19 C18 C17 122.7(11) . . ?
C19 C18 H18 118.6 . . ?
C17 C18 H18 118.6 . . ?
C18 C19 C20 119.7(11) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 N1 122.9(10) . . ?
C21 C20 C19 117.8(11) . . ?
N1 C20 C19 119.3(10) . . ?
C20 C21 C22 121.2(11) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C17 C22 C21 122.1(11) . . ?
C17 C22 H22 118.9 . . ?
C21 C22 H22 118.9 . . ?
N1 C23 H23A 109.5 . . ?
N1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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 F2 -0.1(14) . . . . ?
C6 C1 C2 F2 -179.1(10) . . . . ?
F1 C1 C2 C3 179.7(9) . . . . ?
C6 C1 C2 C3 0.7(17) . . . . ?
F2 C2 C3 C4 178.7(9) . . . . ?
C1 C2 C3 C4 -1.1(16) . . . . ?
C2 C3 C4 C5 1.6(16) . . . . ?
C2 C3 C4 F3 179.2(9) . . . . ?
F3 C4 C5 F4 1.0(14) . . . . ?
C3 C4 C5 F4 178.6(9) . . . . ?
F3 C4 C5 C6 -179.2(9) . . . . ?
C3 C4 C5 C6 -1.6(16) . . . . ?
C2 C1 C6 C5 -0.6(16) . . . . ?
F1 C1 C6 C5 -179.6(9) . . . . ?
C2 C1 C6 C7 179.0(10) . . . . ?
F1 C1 C6 C7 0.0(16) . . . . ?
C4 C5 C6 C1 1.0(15) . . . . ?
F4 C5 C6 C1 -179.2(9) . . . . ?
C4 C5 C6 C7 -178.6(10) . . . . ?
F4 C5 C6 C7 1.2(15) . . . . ?
C1 C6 C7 C8 -1.5(18) . . . . ?
C5 C6 C7 C8 178.1(11) . . . . ?
C6 C7 C8 C9 -178.9(10) . . . . ?
C7 C8 C9 C14 -176.1(11) . . . . ?
C7 C8 C9 C10 5.3(17) . . . . ?
C14 C9 C10 C11 -0.5(15) . . . . ?
C8 C9 C10 C11 178.2(9) . . . . ?
C9 C10 C11 C12 -0.6(16) . . . . ?
C10 C11 C12 C13 2.0(16) . . . . ?
C10 C11 C12 C15 -176.5(10) . . . . ?
C11 C12 C13 C14 -2.3(16) . . . . ?
C15 C12 C13 C14 176.1(10) . . . . ?
C10 C9 C14 C13 0.1(16) . . . . ?
C8 C9 C14 C13 -178.5(9) . . . . ?
C12 C13 C14 C9 1.3(16) . . . . ?
C11 C12 C15 C16 170.6(11) . . . . ?
C13 C12 C15 C16 -7.7(18) . . . . ?
C12 C15 C16 C17 -175.3(11) . . . . ?
C15 C16 C17 C22 177.4(11) . . . . ?
C15 C16 C17 C18 -1.5(18) . . . . ?
C22 C17 C18 C19 0.0(16) . . . . ?
C16 C17 C18 C19 179.0(10) . . . . ?
C17 C18 C19 C20 -1.7(17) . . . . ?
C23 N1 C20 C21 177.5(11) . . . . ?
C24 N1 C20 C21 0.0(16) . . . . ?
C23 N1 C20 C19 -2.9(16) . . . . ?
C24 N1 C20 C19 179.6(10) . . . . ?
C18 C19 C20 C21 2.5(16) . . . . ?
C18 C19 C20 N1 -177.2(10) . . . . ?
N1 C20 C21 C22 177.9(10) . . . . ?
C19 C20 C21 C22 -1.8(16) . . . . ?
C18 C17 C22 C21 0.8(16) . . . . ?
C16 C17 C22 C21 -178.3(10) . . . . ?
C20 C21 C22 C17 0.2(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.941
_diffrn_reflns_theta_full        20.81
_diffrn_measured_fraction_theta_full 0.941
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.097
_database_code_depnum_ccdc_archive 'CCDC 961738'
