# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1548960'
_audit_update_record             
;
2017-05-10 deposited with the CCDC.
2017-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H23 F3 N2'
_chemical_formula_weight         516.54

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.937(6)
_cell_length_b                   10.893(7)
_cell_length_c                   24.753(16)
_cell_angle_alpha                81.827(11)
_cell_angle_beta                 84.583(12)
_cell_angle_gamma                81.397(11)
_cell_volume                     2615(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2051
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      23.44

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9828
_exptl_absorpt_correction_T_max  0.9855
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13460
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_sigmaI/netI    0.1048
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         25.00
_reflns_number_total             9115
_reflns_number_gt                4473
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_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)+(0.0080P)²+1.8000P] 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       0.0031(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9115
_refine_ls_number_parameters     704
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1550
_refine_ls_R_factor_gt           0.0846
_refine_ls_wR_factor_ref         0.2163
_refine_ls_wR_factor_gt          0.1907
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
N1 N 0.5842(3) 0.0129(3) 0.85014(11) 0.0516(7) Uani 1 1 d . . .
N2 N -0.0374(4) 0.2411(4) 0.47861(14) 0.0808(11) Uani 1 1 d . . .
N3 N -0.0816(3) 0.5135(3) 0.14557(11) 0.0569(8) Uani 1 1 d . . .
N4 N 0.5361(4) 0.2598(4) 0.51902(14) 0.0833(11) Uani 1 1 d . . .
C1 C 0.6235(4) -0.1107(3) 0.87534(13) 0.0471(9) Uani 1 1 d . . .
C2 C 0.5412(4) -0.2024(3) 0.87565(15) 0.0608(10) Uani 1 1 d . . .
H2 H 0.4600 -0.1830 0.8585 0.073 Uiso 1 1 calc R . .
C3 C 0.5776(5) -0.3213(4) 0.90096(18) 0.0761(12) Uani 1 1 d . . .
H3 H 0.5220 -0.3825 0.9002 0.091 Uiso 1 1 calc R . .
C4 C 0.6955(6) -0.3508(5) 0.92731(19) 0.0870(15) Uani 1 1 d . . .
H4 H 0.7192 -0.4312 0.9451 0.104 Uiso 1 1 calc R . .
C5 C 0.7786(5) -0.2604(5) 0.92719(17) 0.0781(13) Uani 1 1 d . . .
H5 H 0.8595 -0.2801 0.9446 0.094 Uiso 1 1 calc R . .
C6 C 0.7427(4) -0.1416(4) 0.90161(14) 0.0611(10) Uani 1 1 d . . .
H6 H 0.7993 -0.0810 0.9020 0.073 Uiso 1 1 calc R . .
C7 C 0.5795(3) 0.1155(3) 0.88007(13) 0.0474(8) Uani 1 1 d . . .
C8 C 0.5553(4) 0.0988(4) 0.93665(14) 0.0627(11) Uani 1 1 d . . .
H8 H 0.5416 0.0205 0.9549 0.075 Uiso 1 1 calc R . .
C9 C 0.5518(4) 0.1980(4) 0.96577(16) 0.0723(12) Uani 1 1 d . . .
H9 H 0.5380 0.1855 1.0037 0.087 Uiso 1 1 calc R . .
C10 C 0.5682(4) 0.3134(4) 0.93995(17) 0.0707(12) Uani 1 1 d . . .
H10 H 0.5625 0.3802 0.9600 0.085 Uiso 1 1 calc R . .
C11 C 0.5931(4) 0.3319(4) 0.88407(17) 0.0667(11) Uani 1 1 d . . .
H11 H 0.6058 0.4108 0.8661 0.080 Uiso 1 1 calc R . .
C12 C 0.5992(4) 0.2318(3) 0.85471(15) 0.0567(10) Uani 1 1 d . . .
H12 H 0.6171 0.2441 0.8169 0.068 Uiso 1 1 calc R . .
C13 C 0.5293(3) 0.0295(3) 0.79833(13) 0.0458(8) Uani 1 1 d . . .
C14 C 0.5867(4) -0.0446(4) 0.75924(14) 0.0581(10) Uani 1 1 d . . .
H14 H 0.6636 -0.1026 0.7665 0.070 Uiso 1 1 calc R . .
C15 C 0.5319(4) -0.0338(4) 0.70966(14) 0.0577(10) Uani 1 1 d . . .
H15 H 0.5726 -0.0854 0.6841 0.069 Uiso 1 1 calc R . .
C16 C 0.4188(3) 0.0506(3) 0.69645(13) 0.0472(8) Uani 1 1 d . . .
C17 C 0.3637(4) 0.1262(4) 0.73592(15) 0.0616(10) Uani 1 1 d . . .
H17 H 0.2883 0.1857 0.7283 0.074 Uiso 1 1 calc R . .
C18 C 0.4172(4) 0.1160(4) 0.78605(15) 0.0606(10) Uani 1 1 d . . .
H18 H 0.3773 0.1679 0.8116 0.073 Uiso 1 1 calc R . .
C19 C 0.3555(3) 0.0580(3) 0.64410(14) 0.0492(9) Uani 1 1 d . . .
C20 C 0.4057(5) -0.0212(4) 0.60599(19) 0.1015(18) Uani 1 1 d . . .
H20 H 0.4820 -0.0799 0.6134 0.122 Uiso 1 1 calc R . .
C21 C 0.3473(5) -0.0167(5) 0.55764(19) 0.1066(19) Uani 1 1 d . . .
H21 H 0.3847 -0.0727 0.5334 0.128 Uiso 1 1 calc R . .
C22 C 0.2354(4) 0.0681(3) 0.54391(14) 0.0512(9) Uani 1 1 d . . .
C23 C 0.1846(4) 0.1477(4) 0.58116(15) 0.0614(10) Uani 1 1 d . . .
H23 H 0.1086 0.2066 0.5736 0.074 Uiso 1 1 calc R . .
C24 C 0.2437(4) 0.1429(4) 0.62977(15) 0.0645(11) Uani 1 1 d . . .
H24 H 0.2063 0.1994 0.6538 0.077 Uiso 1 1 calc R . .
C25 C 0.1720(3) 0.0731(3) 0.49169(14) 0.0500(9) Uani 1 1 d . . .
C26 C 0.0564(4) 0.1660(4) 0.48369(14) 0.0543(9) Uani 1 1 d . . .
C27 C 0.2144(4) -0.0063(3) 0.45485(14) 0.0588(10) Uani 1 1 d . . .
H27 H 0.2880 -0.0662 0.4646 0.071 Uiso 1 1 calc R . .
C28 C 0.1643(4) -0.0147(4) 0.40187(14) 0.0563(9) Uani 1 1 d . . .
C29 C 0.2046(4) -0.1247(4) 0.37910(16) 0.0732(12) Uani 1 1 d . . .
H29 H 0.2607 -0.1895 0.3979 0.088 Uiso 1 1 calc R . .
C30 C 0.1633(5) -0.1404(5) 0.32906(17) 0.0816(13) Uani 1 1 d . . .
H30 H 0.1901 -0.2156 0.3149 0.098 Uiso 1 1 calc R . .
C31 C 0.0834(4) -0.0455(5) 0.30064(16) 0.0665(11) Uani 1 1 d . . .
C32 C 0.0441(4) 0.0642(5) 0.32165(17) 0.0773(12) Uani 1 1 d . . .
H32 H -0.0105 0.1290 0.3020 0.093 Uiso 1 1 calc R . .
C33 C 0.0844(4) 0.0805(4) 0.37194(16) 0.0700(11) Uani 1 1 d . . .
H33 H 0.0573 0.1563 0.3856 0.084 Uiso 1 1 calc R . .
C34 C 0.0403(7) -0.0492(7) 0.2452(2) 0.112(2) Uani 1 1 d . . .
C35 C -0.1126(3) 0.4193(3) 0.11736(14) 0.0517(9) Uani 1 1 d . . .
C36 C -0.1392(4) 0.3054(4) 0.14482(17) 0.0641(11) Uani 1 1 d . . .
H36 H -0.1377 0.2904 0.1827 0.077 Uiso 1 1 calc R . .
C37 C -0.1683(4) 0.2130(4) 0.1163(2) 0.0821(13) Uani 1 1 d . . .
H37 H -0.1856 0.1362 0.1353 0.098 Uiso 1 1 calc R . .
C38 C -0.1718(5) 0.2339(5) 0.0604(2) 0.0876(15) Uani 1 1 d . . .
H38 H -0.1899 0.1713 0.0413 0.105 Uiso 1 1 calc R . .
C39 C -0.1485(5) 0.3469(5) 0.03324(18) 0.0797(13) Uani 1 1 d . . .
H39 H -0.1540 0.3621 -0.0045 0.096 Uiso 1 1 calc R . .
C40 C -0.1168(4) 0.4401(4) 0.06047(15) 0.0627(10) Uani 1 1 d . . .
H40 H -0.0983 0.5161 0.0411 0.075 Uiso 1 1 calc R . .
C41 C -0.0789(4) 0.6383(4) 0.11951(14) 0.0549(9) Uani 1 1 d . . .
C42 C -0.1904(4) 0.7070(4) 0.09502(17) 0.0721(12) Uani 1 1 d . . .
H42 H -0.2706 0.6723 0.0955 0.087 Uiso 1 1 calc R . .
C43 C -0.1822(6) 0.8280(5) 0.06968(19) 0.0940(15) Uani 1 1 d . . .
H43 H -0.2565 0.8739 0.0525 0.113 Uiso 1 1 calc R . .
C44 C -0.0641(7) 0.8806(5) 0.0699(2) 0.1003(17) Uani 1 1 d . . .
H44 H -0.0593 0.9624 0.0537 0.120 Uiso 1 1 calc R . .
C45 C 0.0448(6) 0.8119(5) 0.0940(2) 0.0893(15) Uani 1 1 d . . .
H45 H 0.1249 0.8466 0.0937 0.107 Uiso 1 1 calc R . .
C46 C 0.0384(4) 0.6930(4) 0.11850(16) 0.0699(11) Uani 1 1 d . . .
H46 H 0.1141 0.6477 0.1349 0.084 Uiso 1 1 calc R . .
C47 C -0.0308(4) 0.4864(4) 0.19832(14) 0.0544(9) Uani 1 1 d . . .
C48 C -0.0824(4) 0.5613(4) 0.23760(16) 0.0727(12) Uani 1 1 d . . .
H48 H -0.1550 0.6242 0.2302 0.087 Uiso 1 1 calc R . .
C49 C -0.0291(4) 0.5450(4) 0.28763(15) 0.0715(12) Uani 1 1 d . . .
H49 H -0.0665 0.5975 0.3133 0.086 Uiso 1 1 calc R . .
C50 C 0.0787(3) 0.4530(3) 0.30111(14) 0.0502(9) Uani 1 1 d . . .
C51 C 0.1269(4) 0.3759(4) 0.26192(15) 0.0621(10) Uani 1 1 d . . .
H51 H 0.1974 0.3111 0.2697 0.074 Uiso 1 1 calc R . .
C52 C 0.0737(4) 0.3920(4) 0.21155(15) 0.0633(11) Uani 1 1 d . . .
H52 H 0.1090 0.3382 0.1861 0.076 Uiso 1 1 calc R . .
C53 C 0.1411(3) 0.4425(3) 0.35402(14) 0.0508(9) Uani 1 1 d . . .
C54 C 0.0891(5) 0.5207(4) 0.39271(18) 0.0935(16) Uani 1 1 d . . .
H54 H 0.0122 0.5789 0.3857 0.112 Uiso 1 1 calc R . .
C55 C 0.1477(5) 0.5144(5) 0.44113(18) 0.0967(17) Uani 1 1 d . . .
H55 H 0.1098 0.5691 0.4659 0.116 Uiso 1 1 calc R . .
C56 C 0.2603(4) 0.4301(3) 0.45427(14) 0.0517(9) Uani 1 1 d . . .
C57 C 0.3127(4) 0.3515(4) 0.41653(15) 0.0641(11) Uani 1 1 d . . .
H57 H 0.3890 0.2928 0.4238 0.077 Uiso 1 1 calc R . .
C58 C 0.2528(4) 0.3587(4) 0.36763(15) 0.0647(11) Uani 1 1 d . . .
H58 H 0.2906 0.3039 0.3429 0.078 Uiso 1 1 calc R . .
C59 C 0.3246(3) 0.4255(3) 0.50631(14) 0.0499(9) Uani 1 1 d . . .
C60 C 0.4421(4) 0.3328(4) 0.51402(14) 0.0563(10) Uani 1 1 d . . .
C61 C 0.2818(4) 0.5036(3) 0.54364(14) 0.0585(10) Uani 1 1 d . . .
H61 H 0.2071 0.5627 0.5344 0.070 Uiso 1 1 calc R . .
C62 C 0.3326(4) 0.5115(4) 0.59628(14) 0.0554(9) Uani 1 1 d . . .
C63 C 0.2914(4) 0.6223(4) 0.61880(16) 0.0792(13) Uani 1 1 d . . .
H63 H 0.2339 0.6863 0.6001 0.095 Uiso 1 1 calc R . .
C64 C 0.3344(5) 0.6389(5) 0.66833(17) 0.0837(13) Uani 1 1 d . . .
H64 H 0.3070 0.7141 0.6825 0.100 Uiso 1 1 calc R . .
C65 C 0.4168(4) 0.5452(4) 0.69638(15) 0.0642(11) Uani 1 1 d . . .
C66 C 0.4564(4) 0.4339(4) 0.67545(17) 0.0754(12) Uani 1 1 d . . .
H66 H 0.5113 0.3695 0.6951 0.091 Uiso 1 1 calc R . .
C67 C 0.4154(4) 0.4168(4) 0.62570(16) 0.0715(12) Uani 1 1 d . . .
H67 H 0.4436 0.3414 0.6118 0.086 Uiso 1 1 calc R . .
C68 C 0.4603(6) 0.5613(6) 0.75058(19) 0.0859(14) Uani 1 1 d . . .
F1 F -0.0787(5) -0.0211(9) 0.23845(16) 0.280(4) Uani 1 1 d . . .
F2 F 0.1043(5) -0.0066(6) 0.20738(12) 0.231(3) Uani 1 1 d . . .
F3 F 0.0458(11) -0.1657(5) 0.2383(2) 0.325(5) Uani 1 1 d . . .
F4 F 0.5884(3) 0.5033(4) 0.75790(11) 0.1335(13) Uani 1 1 d . . .
F5 F 0.3902(3) 0.5056(3) 0.79167(10) 0.1159(11) Uani 1 1 d . . .
F6 F 0.4593(6) 0.6743(4) 0.75782(15) 0.207(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
N1 C1 1.416(4) . ?
N1 C13 1.419(4) . ?
N1 C7 1.419(4) . ?
N2 C26 1.148(4) . ?
N3 C35 1.406(4) . ?
N3 C41 1.422(5) . ?
N3 C47 1.421(4) . ?
N4 C60 1.136(4) . ?
C1 C2 1.381(5) . ?
C1 C6 1.380(5) . ?
C2 C3 1.369(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.365(5) . ?
C7 C8 1.389(4) . ?
C8 C9 1.376(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.352(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.385(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.374(5) . ?
C13 C14 1.376(4) . ?
C14 C15 1.372(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.387(4) . ?
C16 C19 1.480(5) . ?
C17 C18 1.379(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C24 1.374(5) . ?
C19 C20 1.377(5) . ?
C20 C21 1.370(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.371(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.366(5) . ?
C22 C25 1.481(5) . ?
C23 C24 1.379(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C27 1.341(5) . ?
C25 C26 1.422(5) . ?
C27 C28 1.465(5) . ?
C27 H27 0.9300 . ?
C28 C33 1.379(5) . ?
C28 C29 1.385(5) . ?
C29 C30 1.382(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.359(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.360(6) . ?
C31 C34 1.484(6) . ?
C32 C33 1.386(5) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C34 F2 1.161(6) . ?
C34 F1 1.198(8) . ?
C34 F3 1.297(7) . ?
C35 C36 1.377(5) . ?
C35 C40 1.398(5) . ?
C36 C37 1.386(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.375(6) . ?
C37 H37 0.9300 . ?
C38 C39 1.357(6) . ?
C38 H38 0.9300 . ?
C39 C40 1.384(5) . ?
C39 H39 0.9300 . ?
C40 H40 0.9300 . ?
C41 C46 1.383(5) . ?
C41 C42 1.380(5) . ?
C42 C43 1.388(6) . ?
C42 H42 0.9300 . ?
C43 C44 1.381(7) . ?
C43 H43 0.9300 . ?
C44 C45 1.356(7) . ?
C44 H44 0.9300 . ?
C45 C46 1.357(6) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
C47 C52 1.375(5) . ?
C47 C48 1.371(5) . ?
C48 C49 1.371(5) . ?
C48 H48 0.9300 . ?
C49 C50 1.384(5) . ?
C49 H49 0.9300 . ?
C50 C51 1.378(5) . ?
C50 C53 1.484(5) . ?
C51 C52 1.378(5) . ?
C51 H51 0.9300 . ?
C52 H52 0.9300 . ?
C53 C58 1.364(5) . ?
C53 C54 1.384(5) . ?
C54 C55 1.370(5) . ?
C54 H54 0.9300 . ?
C55 C56 1.370(5) . ?
C55 H55 0.9300 . ?
C56 C57 1.371(5) . ?
C56 C59 1.482(5) . ?
C57 C58 1.386(5) . ?
C57 H57 0.9300 . ?
C58 H58 0.9300 . ?
C59 C61 1.342(4) . ?
C59 C60 1.433(5) . ?
C61 C62 1.459(5) . ?
C61 H61 0.9300 . ?
C62 C67 1.385(5) . ?
C62 C63 1.391(5) . ?
C63 C64 1.380(5) . ?
C63 H63 0.9300 . ?
C64 C65 1.361(6) . ?
C64 H64 0.9300 . ?
C65 C66 1.374(6) . ?
C65 C68 1.489(6) . ?
C66 C67 1.378(5) . ?
C66 H66 0.9300 . ?
C67 H67 0.9300 . ?
C68 F6 1.268(6) . ?
C68 F5 1.305(5) . ?
C68 F4 1.350(6) . ?

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
C1 N1 C13 118.3(3) . . ?
C1 N1 C7 120.0(3) . . ?
C13 N1 C7 120.8(3) . . ?
C35 N3 C41 121.5(3) . . ?
C35 N3 C47 122.1(3) . . ?
C41 N3 C47 115.8(3) . . ?
C2 C1 C6 118.4(4) . . ?
C2 C1 N1 120.7(3) . . ?
C6 C1 N1 120.8(3) . . ?
C3 C2 C1 120.8(4) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.4(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.4(5) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 120.7(4) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C12 C7 C8 118.3(3) . . ?
C12 C7 N1 121.6(3) . . ?
C8 C7 N1 120.0(3) . . ?
C9 C8 C7 120.1(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 120.9(4) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 120.0(4) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 119.3(4) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C7 C12 C11 121.4(3) . . ?
C7 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C18 C13 C14 118.3(3) . . ?
C18 C13 N1 122.0(3) . . ?
C14 C13 N1 119.7(3) . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 122.3(3) . . ?
C14 C15 H15 118.8 . . ?
C16 C15 H15 118.8 . . ?
C15 C16 C17 116.2(3) . . ?
C15 C16 C19 122.3(3) . . ?
C17 C16 C19 121.5(3) . . ?
C18 C17 C16 122.2(3) . . ?
C18 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C13 C18 C17 120.2(3) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C24 C19 C20 115.1(3) . . ?
C24 C19 C16 123.3(3) . . ?
C20 C19 C16 121.6(3) . . ?
C21 C20 C19 122.4(4) . . ?
C21 C20 H20 118.8 . . ?
C19 C20 H20 118.8 . . ?
C22 C21 C20 121.9(4) . . ?
C22 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C21 C22 C23 116.4(3) . . ?
C21 C22 C25 122.0(3) . . ?
C23 C22 C25 121.6(3) . . ?
C22 C23 C24 121.5(3) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C19 C24 C23 122.7(3) . . ?
C19 C24 H24 118.7 . . ?
C23 C24 H24 118.7 . . ?
C27 C25 C26 121.0(3) . . ?
C27 C25 C22 123.8(3) . . ?
C26 C25 C22 115.1(3) . . ?
N2 C26 C25 178.3(4) . . ?
C25 C27 C28 130.9(4) . . ?
C25 C27 H27 114.5 . . ?
C28 C27 H27 114.5 . . ?
C33 C28 C29 117.5(3) . . ?
C33 C28 C27 124.8(4) . . ?
C29 C28 C27 117.6(4) . . ?
C28 C29 C30 121.6(4) . . ?
C28 C29 H29 119.2 . . ?
C30 C29 H29 119.2 . . ?
C31 C30 C29 119.7(4) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C30 C31 C32 119.9(4) . . ?
C30 C31 C34 124.3(5) . . ?
C32 C31 C34 115.7(5) . . ?
C31 C32 C33 120.7(4) . . ?
C31 C32 H32 119.6 . . ?
C33 C32 H32 119.6 . . ?
C32 C33 C28 120.5(4) . . ?
C32 C33 H33 119.7 . . ?
C28 C33 H33 119.7 . . ?
F2 C34 F1 109.5(7) . . ?
F2 C34 F3 104.2(7) . . ?
F1 C34 F3 95.8(6) . . ?
F2 C34 C31 118.8(5) . . ?
F1 C34 C31 117.2(5) . . ?
F3 C34 C31 107.9(6) . . ?
C36 C35 C40 118.8(3) . . ?
C36 C35 N3 121.1(3) . . ?
C40 C35 N3 120.1(3) . . ?
C35 C36 C37 120.4(4) . . ?
C35 C36 H36 119.8 . . ?
C37 C36 H36 119.8 . . ?
C38 C37 C36 120.5(5) . . ?
C38 C37 H37 119.7 . . ?
C36 C37 H37 119.7 . . ?
C39 C38 C37 119.3(4) . . ?
C39 C38 H38 120.4 . . ?
C37 C38 H38 120.4 . . ?
C38 C39 C40 121.4(4) . . ?
C38 C39 H39 119.3 . . ?
C40 C39 H39 119.3 . . ?
C39 C40 C35 119.5(4) . . ?
C39 C40 H40 120.2 . . ?
C35 C40 H40 120.2 . . ?
C46 C41 C42 118.7(4) . . ?
C46 C41 N3 119.4(4) . . ?
C42 C41 N3 121.9(4) . . ?
C43 C42 C41 119.7(4) . . ?
C43 C42 H42 120.2 . . ?
C41 C42 H42 120.2 . . ?
C42 C43 C44 120.3(5) . . ?
C42 C43 H43 119.9 . . ?
C44 C43 H43 119.9 . . ?
C45 C44 C43 119.4(5) . . ?
C45 C44 H44 120.3 . . ?
C43 C44 H44 120.3 . . ?
C46 C45 C44 120.8(5) . . ?
C46 C45 H45 119.6 . . ?
C44 C45 H45 119.6 . . ?
C45 C46 C41 121.1(4) . . ?
C45 C46 H46 119.4 . . ?
C41 C46 H46 119.4 . . ?
C52 C47 C48 117.6(3) . . ?
C52 C47 N3 123.3(3) . . ?
C48 C47 N3 119.1(4) . . ?
C49 C48 C47 121.2(4) . . ?
C49 C48 H48 119.4 . . ?
C47 C48 H48 119.4 . . ?
C48 C49 C50 122.1(3) . . ?
C48 C49 H49 119.0 . . ?
C50 C49 H49 119.0 . . ?
C49 C50 C51 116.1(3) . . ?
C49 C50 C53 121.2(3) . . ?
C51 C50 C53 122.6(3) . . ?
C52 C51 C50 122.0(4) . . ?
C52 C51 H51 119.0 . . ?
C50 C51 H51 119.0 . . ?
C47 C52 C51 121.0(3) . . ?
C47 C52 H52 119.5 . . ?
C51 C52 H52 119.5 . . ?
C58 C53 C54 115.6(3) . . ?
C58 C53 C50 123.3(3) . . ?
C54 C53 C50 121.0(3) . . ?
C55 C54 C53 121.7(4) . . ?
C55 C54 H54 119.1 . . ?
C53 C54 H54 119.1 . . ?
C54 C55 C56 122.1(4) . . ?
C54 C55 H55 118.9 . . ?
C56 C55 H55 118.9 . . ?
C55 C56 C57 116.9(3) . . ?
C55 C56 C59 121.8(3) . . ?
C57 C56 C59 121.3(3) . . ?
C56 C57 C58 120.5(4) . . ?
C56 C57 H57 119.7 . . ?
C58 C57 H57 119.7 . . ?
C53 C58 C57 123.1(3) . . ?
C53 C58 H58 118.5 . . ?
C57 C58 H58 118.5 . . ?
C61 C59 C60 120.7(3) . . ?
C61 C59 C56 124.1(3) . . ?
C60 C59 C56 115.2(3) . . ?
N4 C60 C59 178.6(4) . . ?
C59 C61 C62 130.9(4) . . ?
C59 C61 H61 114.5 . . ?
C62 C61 H61 114.5 . . ?
C67 C62 C63 118.0(4) . . ?
C67 C62 C61 125.1(3) . . ?
C63 C62 C61 116.8(3) . . ?
C64 C63 C62 121.2(4) . . ?
C64 C63 H63 119.4 . . ?
C62 C63 H63 119.4 . . ?
C65 C64 C63 119.9(4) . . ?
C65 C64 H64 120.0 . . ?
C63 C64 H64 120.0 . . ?
C64 C65 C66 119.9(4) . . ?
C64 C65 C68 120.1(4) . . ?
C66 C65 C68 119.9(4) . . ?
C67 C66 C65 120.7(4) . . ?
C67 C66 H66 119.7 . . ?
C65 C66 H66 119.7 . . ?
C66 C67 C62 120.3(4) . . ?
C66 C67 H67 119.9 . . ?
C62 C67 H67 119.9 . . ?
F6 C68 F5 108.8(5) . . ?
F6 C68 F4 106.5(5) . . ?
F5 C68 F4 102.0(4) . . ?
F6 C68 C65 114.3(4) . . ?
F5 C68 C65 113.1(4) . . ?
F4 C68 C65 111.2(4) . . ?

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
C13 N1 C1 C2 -43.7(4) . . . . ?
C7 N1 C1 C2 126.2(3) . . . . ?
C13 N1 C1 C6 138.4(3) . . . . ?
C7 N1 C1 C6 -51.8(4) . . . . ?
C6 C1 C2 C3 -0.7(5) . . . . ?
N1 C1 C2 C3 -178.7(3) . . . . ?
C1 C2 C3 C4 1.2(6) . . . . ?
C2 C3 C4 C5 -1.3(7) . . . . ?
C3 C4 C5 C6 0.9(6) . . . . ?
C4 C5 C6 C1 -0.4(6) . . . . ?
C2 C1 C6 C5 0.2(5) . . . . ?
N1 C1 C6 C5 178.2(3) . . . . ?
C1 N1 C7 C12 152.1(3) . . . . ?
C13 N1 C7 C12 -38.3(5) . . . . ?
C1 N1 C7 C8 -27.4(5) . . . . ?
C13 N1 C7 C8 142.2(3) . . . . ?
C12 C7 C8 C9 0.0(6) . . . . ?
N1 C7 C8 C9 179.5(4) . . . . ?
C7 C8 C9 C10 1.7(7) . . . . ?
C8 C9 C10 C11 -2.1(7) . . . . ?
C9 C10 C11 C12 1.0(6) . . . . ?
C8 C7 C12 C11 -1.2(6) . . . . ?
N1 C7 C12 C11 179.4(3) . . . . ?
C10 C11 C12 C7 0.7(6) . . . . ?
C1 N1 C13 C18 136.8(4) . . . . ?
C7 N1 C13 C18 -33.0(5) . . . . ?
C1 N1 C13 C14 -41.6(4) . . . . ?
C7 N1 C13 C14 148.6(3) . . . . ?
C18 C13 C14 C15 -1.2(5) . . . . ?
N1 C13 C14 C15 177.3(3) . . . . ?
C13 C14 C15 C16 0.3(6) . . . . ?
C14 C15 C16 C17 0.9(6) . . . . ?
C14 C15 C16 C19 -176.9(3) . . . . ?
C15 C16 C17 C18 -1.3(6) . . . . ?
C19 C16 C17 C18 176.6(3) . . . . ?
C14 C13 C18 C17 0.8(6) . . . . ?
N1 C13 C18 C17 -177.6(3) . . . . ?
C16 C17 C18 C13 0.4(6) . . . . ?
C15 C16 C19 C24 -179.0(4) . . . . ?
C17 C16 C19 C24 3.2(6) . . . . ?
C15 C16 C19 C20 1.1(6) . . . . ?
C17 C16 C19 C20 -176.6(4) . . . . ?
C24 C19 C20 C21 -0.8(8) . . . . ?
C16 C19 C20 C21 179.1(5) . . . . ?
C19 C20 C21 C22 0.5(9) . . . . ?
C20 C21 C22 C23 -0.2(8) . . . . ?
C20 C21 C22 C25 -179.9(5) . . . . ?
C21 C22 C23 C24 0.2(6) . . . . ?
C25 C22 C23 C24 180.0(4) . . . . ?
C20 C19 C24 C23 0.8(6) . . . . ?
C16 C19 C24 C23 -179.1(4) . . . . ?
C22 C23 C24 C19 -0.5(7) . . . . ?
C21 C22 C25 C27 2.6(6) . . . . ?
C23 C22 C25 C27 -177.1(4) . . . . ?
C21 C22 C25 C26 179.8(4) . . . . ?
C23 C22 C25 C26 0.1(5) . . . . ?
C27 C25 C26 N2 158(14) . . . . ?
C22 C25 C26 N2 -19(15) . . . . ?
C26 C25 C27 C28 3.0(6) . . . . ?
C22 C25 C27 C28 -180.0(4) . . . . ?
C25 C27 C28 C33 18.9(7) . . . . ?
C25 C27 C28 C29 -163.8(4) . . . . ?
C33 C28 C29 C30 -1.9(6) . . . . ?
C27 C28 C29 C30 -179.4(4) . . . . ?
C28 C29 C30 C31 1.3(7) . . . . ?
C29 C30 C31 C32 -0.2(7) . . . . ?
C29 C30 C31 C34 176.1(4) . . . . ?
C30 C31 C32 C33 -0.1(6) . . . . ?
C34 C31 C32 C33 -176.8(4) . . . . ?
C31 C32 C33 C28 -0.6(6) . . . . ?
C29 C28 C33 C32 1.5(6) . . . . ?
C27 C28 C33 C32 178.8(4) . . . . ?
C30 C31 C34 F2 -94.7(8) . . . . ?
C32 C31 C34 F2 81.8(8) . . . . ?
C30 C31 C34 F1 130.1(8) . . . . ?
C32 C31 C34 F1 -53.4(9) . . . . ?
C30 C31 C34 F3 23.5(9) . . . . ?
C32 C31 C34 F3 -160.0(7) . . . . ?
C41 N3 C35 C36 -168.2(3) . . . . ?
C47 N3 C35 C36 21.9(5) . . . . ?
C41 N3 C35 C40 11.9(5) . . . . ?
C47 N3 C35 C40 -158.0(3) . . . . ?
C40 C35 C36 C37 0.6(6) . . . . ?
N3 C35 C36 C37 -179.4(3) . . . . ?
C35 C36 C37 C38 -0.4(6) . . . . ?
C36 C37 C38 C39 -1.0(7) . . . . ?
C37 C38 C39 C40 2.2(7) . . . . ?
C38 C39 C40 C35 -2.0(6) . . . . ?
C36 C35 C40 C39 0.6(5) . . . . ?
N3 C35 C40 C39 -179.5(3) . . . . ?
C35 N3 C41 C46 -123.3(4) . . . . ?
C47 N3 C41 C46 47.2(4) . . . . ?
C35 N3 C41 C42 56.7(5) . . . . ?
C47 N3 C41 C42 -132.8(4) . . . . ?
C46 C41 C42 C43 0.6(6) . . . . ?
N3 C41 C42 C43 -179.4(3) . . . . ?
C41 C42 C43 C44 -1.3(7) . . . . ?
C42 C43 C44 C45 1.5(7) . . . . ?
C43 C44 C45 C46 -1.0(8) . . . . ?
C44 C45 C46 C41 0.2(7) . . . . ?
C42 C41 C46 C45 0.0(6) . . . . ?
N3 C41 C46 C45 180.0(4) . . . . ?
C35 N3 C47 C52 47.0(5) . . . . ?
C41 N3 C47 C52 -123.5(4) . . . . ?
C35 N3 C47 C48 -136.6(4) . . . . ?
C41 N3 C47 C48 53.0(5) . . . . ?
C52 C47 C48 C49 1.9(6) . . . . ?
N3 C47 C48 C49 -174.7(4) . . . . ?
C47 C48 C49 C50 -0.1(7) . . . . ?
C48 C49 C50 C51 -1.9(6) . . . . ?
C48 C49 C50 C53 175.8(4) . . . . ?
C49 C50 C51 C52 2.0(6) . . . . ?
C53 C50 C51 C52 -175.7(3) . . . . ?
C48 C47 C52 C51 -1.8(6) . . . . ?
N3 C47 C52 C51 174.6(3) . . . . ?
C50 C51 C52 C47 -0.1(6) . . . . ?
C49 C50 C53 C58 -175.7(4) . . . . ?
C51 C50 C53 C58 1.9(6) . . . . ?
C49 C50 C53 C54 3.2(6) . . . . ?
C51 C50 C53 C54 -179.3(4) . . . . ?
C58 C53 C54 C55 0.7(7) . . . . ?
C50 C53 C54 C55 -178.2(4) . . . . ?
C53 C54 C55 C56 -0.5(9) . . . . ?
C54 C55 C56 C57 0.1(8) . . . . ?
C54 C55 C56 C59 178.9(4) . . . . ?
C55 C56 C57 C58 0.1(6) . . . . ?
C59 C56 C57 C58 -178.7(4) . . . . ?
C54 C53 C58 C57 -0.6(6) . . . . ?
C50 C53 C58 C57 178.3(4) . . . . ?
C56 C57 C58 C53 0.2(6) . . . . ?
C55 C56 C59 C61 -1.8(6) . . . . ?
C57 C56 C59 C61 176.9(4) . . . . ?
C55 C56 C59 C60 -179.6(4) . . . . ?
C57 C56 C59 C60 -0.9(5) . . . . ?
C61 C59 C60 N4 -138(18) . . . . ?
C56 C59 C60 N4 40(18) . . . . ?
C60 C59 C61 C62 -2.5(6) . . . . ?
C56 C59 C61 C62 179.8(4) . . . . ?
C59 C61 C62 C67 -18.5(7) . . . . ?
C59 C61 C62 C63 163.0(4) . . . . ?
C67 C62 C63 C64 1.6(6) . . . . ?
C61 C62 C63 C64 -179.8(4) . . . . ?
C62 C63 C64 C65 -1.0(7) . . . . ?
C63 C64 C65 C66 -0.4(7) . . . . ?
C63 C64 C65 C68 -178.3(4) . . . . ?
C64 C65 C66 C67 1.2(7) . . . . ?
C68 C65 C66 C67 179.1(4) . . . . ?
C65 C66 C67 C62 -0.6(7) . . . . ?
C63 C62 C67 C66 -0.8(6) . . . . ?
C61 C62 C67 C66 -179.3(4) . . . . ?
C64 C65 C68 F6 -24.6(7) . . . . ?
C66 C65 C68 F6 157.5(5) . . . . ?
C64 C65 C68 F5 100.7(6) . . . . ?
C66 C65 C68 F5 -77.2(6) . . . . ?
C64 C65 C68 F4 -145.3(5) . . . . ?
C66 C65 C68 F4 36.9(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1548959'
_audit_update_record             
;
2017-05-10 deposited with the CCDC.
2017-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H23 F3 N2'
_chemical_formula_weight         516.54

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

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

_cell_length_a                   12.565(9)
_cell_length_b                   8.465(6)
_cell_length_c                   26.031(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.084(14)
_cell_angle_gamma                90.00
_cell_volume                     2741(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1888
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      21.33

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9802
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13127
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_sigmaI/netI    0.0693
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4794
_reflns_number_gt                2439
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_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)+(0.0100P)²+3.0000P] 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       0.0027(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4794
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1429
_refine_ls_R_factor_gt           0.0814
_refine_ls_wR_factor_ref         0.1683
_refine_ls_wR_factor_gt          0.1511
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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 0.0597(5) -0.4165(4) 0.10290(19) 0.223(3) Uani 1 1 d . . .
F2 F -0.0560(4) -0.3179(5) 0.1324(2) 0.239(3) Uani 1 1 d . . .
F3 F 0.0857(6) -0.3125(6) 0.17145(18) 0.303(4) Uani 1 1 d . . .
N1 N 0.8848(2) 0.3651(3) 0.28762(11) 0.0633(8) Uani 1 1 d . . .
N2 N 0.2086(4) 0.6173(6) -0.03240(18) 0.1300(17) Uani 1 1 d . . .
C1 C 0.9842(3) 0.3283(4) 0.27039(13) 0.0598(9) Uani 1 1 d . . .
C2 C 0.9899(3) 0.2054(5) 0.23592(15) 0.0747(11) Uani 1 1 d . . .
H2 H 0.9285 0.1480 0.2236 0.090 Uiso 1 1 calc R . .
C3 C 1.0863(4) 0.1682(6) 0.21995(17) 0.0962(15) Uani 1 1 d . . .
H3 H 1.0894 0.0857 0.1966 0.115 Uiso 1 1 calc R . .
C4 C 1.1770(4) 0.2492(8) 0.2375(2) 0.1077(17) Uani 1 1 d . . .
H4 H 1.2418 0.2229 0.2263 0.129 Uiso 1 1 calc R . .
C5 C 1.1719(4) 0.3703(7) 0.2719(2) 0.1085(17) Uani 1 1 d . . .
H5 H 1.2341 0.4253 0.2846 0.130 Uiso 1 1 calc R . .
C6 C 1.0757(3) 0.4118(5) 0.28779(17) 0.0855(13) Uani 1 1 d . . .
H6 H 1.0728 0.4964 0.3103 0.103 Uiso 1 1 calc R . .
C7 C 0.8834(3) 0.3919(4) 0.34149(14) 0.0619(10) Uani 1 1 d . . .
C8 C 0.9509(4) 0.3070(5) 0.37811(16) 0.0834(12) Uani 1 1 d . . .
H8 H 0.9956 0.2299 0.3673 0.100 Uiso 1 1 calc R . .
C9 C 0.9527(5) 0.3354(7) 0.43019(18) 0.1085(17) Uani 1 1 d . . .
H9 H 0.9995 0.2796 0.4545 0.130 Uiso 1 1 calc R . .
C10 C 0.8852(5) 0.4464(7) 0.44610(19) 0.1099(18) Uani 1 1 d . . .
H10 H 0.8858 0.4647 0.4814 0.132 Uiso 1 1 calc R . .
C11 C 0.8162(4) 0.5315(6) 0.4106(2) 0.0943(14) Uani 1 1 d . . .
H11 H 0.7702 0.6059 0.4219 0.113 Uiso 1 1 calc R . .
C12 C 0.8157(3) 0.5057(5) 0.35765(15) 0.0718(11) Uani 1 1 d . . .
H12 H 0.7704 0.5640 0.3334 0.086 Uiso 1 1 calc R . .
C13 C 0.7894(3) 0.3669(4) 0.25181(14) 0.0557(9) Uani 1 1 d . . .
C14 C 0.7899(3) 0.4238(4) 0.20156(14) 0.0620(10) Uani 1 1 d . . .
H14 H 0.8537 0.4607 0.1916 0.074 Uiso 1 1 calc R . .
C15 C 0.6974(3) 0.4261(4) 0.16665(14) 0.0607(9) Uani 1 1 d . . .
H15 H 0.6999 0.4659 0.1335 0.073 Uiso 1 1 calc R . .
C16 C 0.6000(3) 0.3707(4) 0.17918(13) 0.0547(9) Uani 1 1 d . . .
C17 C 0.6016(3) 0.3140(4) 0.22965(13) 0.0588(9) Uani 1 1 d . . .
H17 H 0.5383 0.2760 0.2397 0.071 Uiso 1 1 calc R . .
C18 C 0.6933(3) 0.3125(4) 0.26471(14) 0.0602(9) Uani 1 1 d . . .
H18 H 0.6908 0.2741 0.2980 0.072 Uiso 1 1 calc R . .
C19 C 0.5004(3) 0.3710(4) 0.14117(13) 0.0567(9) Uani 1 1 d . . .
C20 C 0.5032(3) 0.3738(5) 0.08783(14) 0.0694(11) Uani 1 1 d . . .
H20 H 0.5692 0.3723 0.0756 0.083 Uiso 1 1 calc R . .
C21 C 0.4098(3) 0.3786(5) 0.05279(14) 0.0741(11) Uani 1 1 d . . .
H21 H 0.4146 0.3859 0.0175 0.089 Uiso 1 1 calc R . .
C22 C 0.3106(3) 0.3731(4) 0.06864(14) 0.0651(10) Uani 1 1 d . . .
C23 C 0.3068(3) 0.3694(5) 0.12178(14) 0.0789(12) Uani 1 1 d . . .
H23 H 0.2406 0.3665 0.1339 0.095 Uiso 1 1 calc R . .
C24 C 0.3998(3) 0.3701(5) 0.15658(14) 0.0728(11) Uani 1 1 d . . .
H24 H 0.3947 0.3699 0.1919 0.087 Uiso 1 1 calc R . .
C25 C 0.2107(3) 0.3816(5) 0.03076(14) 0.0727(11) Uani 1 1 d . . .
C26 C 0.2085(4) 0.5115(6) -0.00498(18) 0.0926(14) Uani 1 1 d . . .
C27 C 0.1240(3) 0.2883(5) 0.02710(15) 0.0782(12) Uani 1 1 d . . .
H27 H 0.0655 0.3209 0.0036 0.094 Uiso 1 1 calc R . .
C28 C 0.1084(3) 0.1412(5) 0.05516(14) 0.0743(11) Uani 1 1 d . . .
C29 C 0.1896(3) 0.0336(5) 0.07021(16) 0.0847(13) Uani 1 1 d . . .
H29 H 0.2593 0.0567 0.0644 0.102 Uiso 1 1 calc R . .
C30 C 0.1692(4) -0.1086(6) 0.09384(16) 0.0905(13) Uani 1 1 d . . .
H30 H 0.2249 -0.1792 0.1040 0.109 Uiso 1 1 calc R . .
C31 C 0.0649(4) -0.1447(5) 0.10219(15) 0.0785(12) Uani 1 1 d . . .
C32 C -0.0149(4) -0.0398(6) 0.08836(18) 0.0941(14) Uani 1 1 d . . .
H32 H -0.0840 -0.0617 0.0953 0.113 Uiso 1 1 calc R . .
C33 C 0.0055(4) 0.1017(6) 0.06366(17) 0.0924(14) Uani 1 1 d . . .
H33 H -0.0510 0.1702 0.0528 0.111 Uiso 1 1 calc R . .
C34 C 0.0425(6) -0.2938(7) 0.1263(3) 0.1139(18) 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
F1 C34 1.239(6) . ?
F2 C34 1.286(6) . ?
F3 C34 1.233(7) . ?
N1 C13 1.411(4) . ?
N1 C1 1.419(4) . ?
N1 C7 1.423(4) . ?
N2 C26 1.145(5) . ?
C1 C6 1.371(5) . ?
C1 C2 1.382(5) . ?
C2 C3 1.371(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.353(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.389(5) . ?
C7 C8 1.385(5) . ?
C8 C9 1.374(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.369(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.378(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.394(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.378(4) . ?
C13 C14 1.395(5) . ?
C14 C15 1.371(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.392(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.396(4) . ?
C16 C19 1.482(5) . ?
C17 C18 1.365(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C24 1.379(5) . ?
C19 C20 1.394(4) . ?
C20 C21 1.381(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.368(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.391(5) . ?
C22 C25 1.485(5) . ?
C23 C24 1.375(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C27 1.338(5) . ?
C25 C26 1.438(6) . ?
C27 C28 1.470(5) . ?
C27 H27 0.9300 . ?
C28 C33 1.383(5) . ?
C28 C29 1.383(5) . ?
C29 C30 1.393(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.391(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.350(6) . ?
C31 C34 1.455(6) . ?
C32 C33 1.400(6) . ?
C32 H32 0.9300 . ?
C33 H33 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
C13 N1 C1 119.8(3) . . ?
C13 N1 C7 121.5(3) . . ?
C1 N1 C7 118.7(3) . . ?
C6 C1 C2 119.0(4) . . ?
C6 C1 N1 121.1(4) . . ?
C2 C1 N1 119.9(3) . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 121.3(5) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 119.0(5) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C4 C5 C6 120.8(5) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 120.0(4) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C12 C7 C8 119.6(4) . . ?
C12 C7 N1 120.2(4) . . ?
C8 C7 N1 120.3(4) . . ?
C7 C8 C9 120.8(4) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 119.6(5) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 120.9(5) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 119.8(5) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C11 119.3(4) . . ?
C7 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
N1 C13 C18 121.9(3) . . ?
N1 C13 C14 120.5(3) . . ?
C18 C13 C14 117.6(3) . . ?
C15 C14 C13 120.8(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 122.1(3) . . ?
C16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C15 C16 C17 116.0(3) . . ?
C15 C16 C19 122.1(3) . . ?
C17 C16 C19 121.9(3) . . ?
C18 C17 C16 122.1(3) . . ?
C18 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C17 C18 C13 121.4(3) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
C24 C19 C20 116.2(3) . . ?
C24 C19 C16 121.9(3) . . ?
C20 C19 C16 121.9(3) . . ?
C21 C20 C19 121.4(3) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C22 C21 C20 121.7(4) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C23 117.5(4) . . ?
C21 C22 C25 121.3(3) . . ?
C23 C22 C25 121.1(3) . . ?
C24 C23 C22 120.7(4) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C19 122.5(3) . . ?
C23 C24 H24 118.7 . . ?
C19 C24 H24 118.7 . . ?
C27 C25 C26 117.6(4) . . ?
C27 C25 C22 128.5(4) . . ?
C26 C25 C22 113.8(4) . . ?
N2 C26 C25 178.1(5) . . ?
C25 C27 C28 128.9(4) . . ?
C25 C27 H27 115.5 . . ?
C28 C27 H27 115.5 . . ?
C33 C28 C29 117.7(4) . . ?
C33 C28 C27 118.5(4) . . ?
C29 C28 C27 123.6(4) . . ?
C28 C29 C30 121.3(4) . . ?
C28 C29 H29 119.3 . . ?
C30 C29 H29 119.3 . . ?
C31 C30 C29 119.7(4) . . ?
C31 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
C32 C31 C30 119.6(4) . . ?
C32 C31 C34 120.3(5) . . ?
C30 C31 C34 120.1(5) . . ?
C31 C32 C33 120.5(4) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 H32 119.7 . . ?
C28 C33 C32 121.1(4) . . ?
C28 C33 H33 119.5 . . ?
C32 C33 H33 119.5 . . ?
F3 C34 F1 106.1(6) . . ?
F3 C34 F2 99.5(6) . . ?
F1 C34 F2 99.5(6) . . ?
F3 C34 C31 115.9(6) . . ?
F1 C34 C31 117.2(5) . . ?
F2 C34 C31 116.0(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
C13 N1 C1 C6 137.8(4) . . . . ?
C7 N1 C1 C6 -45.2(5) . . . . ?
C13 N1 C1 C2 -42.9(5) . . . . ?
C7 N1 C1 C2 134.1(4) . . . . ?
C6 C1 C2 C3 0.4(6) . . . . ?
N1 C1 C2 C3 -178.9(4) . . . . ?
C1 C2 C3 C4 0.4(7) . . . . ?
C2 C3 C4 C5 0.1(8) . . . . ?
C3 C4 C5 C6 -1.2(8) . . . . ?
C2 C1 C6 C5 -1.5(6) . . . . ?
N1 C1 C6 C5 177.8(4) . . . . ?
C4 C5 C6 C1 2.0(7) . . . . ?
C13 N1 C7 C12 -39.5(5) . . . . ?
C1 N1 C7 C12 143.6(3) . . . . ?
C13 N1 C7 C8 141.8(4) . . . . ?
C1 N1 C7 C8 -35.2(5) . . . . ?
C12 C7 C8 C9 -0.9(6) . . . . ?
N1 C7 C8 C9 177.9(4) . . . . ?
C7 C8 C9 C10 1.5(7) . . . . ?
C8 C9 C10 C11 -0.8(8) . . . . ?
C9 C10 C11 C12 -0.6(8) . . . . ?
C8 C7 C12 C11 -0.5(6) . . . . ?
N1 C7 C12 C11 -179.3(3) . . . . ?
C10 C11 C12 C7 1.3(6) . . . . ?
C1 N1 C13 C18 142.2(3) . . . . ?
C7 N1 C13 C18 -34.8(5) . . . . ?
C1 N1 C13 C14 -37.5(5) . . . . ?
C7 N1 C13 C14 145.6(3) . . . . ?
N1 C13 C14 C15 -179.9(3) . . . . ?
C18 C13 C14 C15 0.4(5) . . . . ?
C13 C14 C15 C16 -0.8(5) . . . . ?
C14 C15 C16 C17 0.6(5) . . . . ?
C14 C15 C16 C19 -179.1(3) . . . . ?
C15 C16 C17 C18 -0.1(5) . . . . ?
C19 C16 C17 C18 179.6(3) . . . . ?
C16 C17 C18 C13 -0.3(5) . . . . ?
N1 C13 C18 C17 -179.6(3) . . . . ?
C14 C13 C18 C17 0.1(5) . . . . ?
C15 C16 C19 C24 -157.0(4) . . . . ?
C17 C16 C19 C24 23.4(5) . . . . ?
C15 C16 C19 C20 22.4(5) . . . . ?
C17 C16 C19 C20 -157.2(3) . . . . ?
C24 C19 C20 C21 1.3(6) . . . . ?
C16 C19 C20 C21 -178.1(3) . . . . ?
C19 C20 C21 C22 -3.3(6) . . . . ?
C20 C21 C22 C23 2.8(6) . . . . ?
C20 C21 C22 C25 178.8(4) . . . . ?
C21 C22 C23 C24 -0.5(6) . . . . ?
C25 C22 C23 C24 -176.5(4) . . . . ?
C22 C23 C24 C19 -1.4(7) . . . . ?
C20 C19 C24 C23 1.0(6) . . . . ?
C16 C19 C24 C23 -179.6(4) . . . . ?
C21 C22 C25 C27 131.5(5) . . . . ?
C23 C22 C25 C27 -52.8(6) . . . . ?
C21 C22 C25 C26 -50.6(5) . . . . ?
C23 C22 C25 C26 125.2(4) . . . . ?
C27 C25 C26 N2 149(18) . . . . ?
C22 C25 C26 N2 -29(18) . . . . ?
C26 C25 C27 C28 174.1(4) . . . . ?
C22 C25 C27 C28 -8.0(7) . . . . ?
C25 C27 C28 C33 151.6(5) . . . . ?
C25 C27 C28 C29 -33.5(7) . . . . ?
C33 C28 C29 C30 -1.0(6) . . . . ?
C27 C28 C29 C30 -175.9(4) . . . . ?
C28 C29 C30 C31 0.6(7) . . . . ?
C29 C30 C31 C32 -1.5(7) . . . . ?
C29 C30 C31 C34 179.3(5) . . . . ?
C30 C31 C32 C33 2.8(7) . . . . ?
C34 C31 C32 C33 -178.0(5) . . . . ?
C29 C28 C33 C32 2.3(7) . . . . ?
C27 C28 C33 C32 177.5(4) . . . . ?
C31 C32 C33 C28 -3.3(7) . . . . ?
C32 C31 C34 F3 -115.1(8) . . . . ?
C30 C31 C34 F3 64.1(8) . . . . ?
C32 C31 C34 F1 118.3(7) . . . . ?
C30 C31 C34 F1 -62.5(8) . . . . ?
C32 C31 C34 F2 1.2(9) . . . . ?
C30 C31 C34 F2 -179.7(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.043
