# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            Naphthalenebishydraziimide
_chemical_melting_point          ?
_chemical_formula_moiety         ' C28 H14 F6 N4 O4, 4(C4 H8 O)'
_chemical_formula_sum            'C44 H46 F6 N4 O8'
_chemical_formula_weight         872.85

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 21/c'
_symmetry_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                   12.939(5)
_cell_length_b                   16.079(6)
_cell_length_c                   10.585(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.796(11)
_cell_angle_gamma                90.00
_cell_volume                     2186.8(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2086
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      21.33

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7452
_exptl_absorpt_correction_T_max  0.8872
_exptl_absorpt_process_details   
;
SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction  
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14031
_diffrn_reflns_av_R_equivalents  0.0815
_diffrn_reflns_av_sigmaI/netI    0.1154
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         25.46
_reflns_number_total             3964
_reflns_number_gt                2163
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR-92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
;
 Refinement showed high disorder in the terminal -CF3 group which could be
resolved by splitting each F on two positions with their site occupancies
and uiso being refined as free variables. Two tetrahydrofuran  molecules 
were also located as solvent molecules in the asymmetric unit with some
degree of disorder which could not be resolved. The final difference Fourier
showed no significant residual electron density. The crystal structure showed
SAV of 35 A**3 which are due to the packing forces.    
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.1568P)^2^+19.6384P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3964
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2018
_refine_ls_R_factor_gt           0.1315
_refine_ls_wR_factor_ref         0.3870
_refine_ls_wR_factor_gt          0.3415
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_restrained_S_all      0.976
_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
C1 C 0.0475(9) 0.2007(8) 0.3419(9) 0.061(3) Uani 1 1 d . . .
C2 C 0.1536(7) 0.1811(6) 0.4024(9) 0.048(2) Uani 1 1 d . A .
C3 C 0.1697(7) 0.1631(5) 0.5291(8) 0.042(2) Uani 1 1 d . . .
H3 H 0.1120 0.1631 0.5769 0.051 Uiso 1 1 calc R A .
C4 C 0.2674(6) 0.1447(5) 0.5901(7) 0.0331(18) Uani 1 1 d . A .
H4 H 0.2770 0.1330 0.6787 0.040 Uiso 1 1 calc R . .
C5 C 0.3510(6) 0.1438(4) 0.5197(7) 0.0281(16) Uani 1 1 d . . .
C6 C 0.3355(6) 0.1623(5) 0.3902(7) 0.0333(18) Uani 1 1 d . A .
H6 H 0.3930 0.1619 0.3420 0.040 Uiso 1 1 calc R . .
C7 C 0.2378(6) 0.1812(5) 0.3316(7) 0.0368(19) Uani 1 1 d . . .
H7 H 0.2277 0.1942 0.2435 0.044 Uiso 1 1 calc R A .
C8 C 0.4526(5) 0.0045(4) 0.7018(7) 0.0241(15) Uani 1 1 d . A .
C9 C 0.4683(5) -0.0324(4) 0.8313(7) 0.0264(16) Uani 1 1 d . . .
C10 C 0.4938(5) 0.0180(4) 0.9381(6) 0.0216(15) Uani 1 1 d . . .
C11 C 0.5074(5) 0.1056(4) 0.9292(6) 0.0229(15) Uani 1 1 d . . .
C12 C 0.4945(5) 0.1439(4) 0.7986(7) 0.0252(16) Uani 1 1 d . A .
C13 C 0.5300(6) 0.1543(4) 1.0347(6) 0.0270(16) Uani 1 1 d . . .
H13 H 0.5357 0.2129 1.0263 0.032 Uiso 1 1 calc R . .
C14 C 0.4552(5) -0.1173(4) 0.8442(7) 0.0265(16) Uani 1 1 d . . .
H14 H 0.4362 -0.1506 0.7711 0.032 Uiso 1 1 calc R . .
C15 C 0.8000(9) 0.0028(7) 0.1591(14) 0.081(4) Uani 1 1 d . . .
H15B H 0.7587 0.0543 0.1426 0.097 Uiso 1 1 calc R . .
H15A H 0.8294 0.0022 0.2498 0.097 Uiso 1 1 calc R . .
C16 C 0.8788(17) 0.0002(16) 0.0826(17) 0.183(12) Uani 1 1 d . . .
H16B H 0.9455 -0.0126 0.1348 0.219 Uiso 1 1 calc R . .
H16A H 0.8856 0.0553 0.0424 0.219 Uiso 1 1 calc R . .
C17 C 0.8569(9) -0.0634(10) -0.0163(11) 0.095(5) Uani 1 1 d . . .
H17B H 0.9093 -0.1085 -0.0062 0.114 Uiso 1 1 calc R . .
H17A H 0.8555 -0.0390 -0.1024 0.114 Uiso 1 1 calc R . .
C18 C 0.7541(7) -0.0937(6) 0.0058(8) 0.052(2) Uani 1 1 d . . .
H18B H 0.6999 -0.0705 -0.0584 0.062 Uiso 1 1 calc R . .
H18A H 0.7515 -0.1551 0.0001 0.062 Uiso 1 1 calc R . .
C19 C 0.7646(9) 0.1637(8) 0.8057(15) 0.091(4) Uani 1 1 d . . .
H19A H 0.8361 0.1532 0.8469 0.109 Uiso 1 1 calc R . .
H19B H 0.7273 0.1982 0.8632 0.109 Uiso 1 1 calc R . .
C20 C 0.7667(10) 0.2051(8) 0.6826(16) 0.093(5) Uani 1 1 d . . .
H20A H 0.8280 0.2421 0.6845 0.112 Uiso 1 1 calc R . .
H20B H 0.7028 0.2385 0.6604 0.112 Uiso 1 1 calc R . .
C21 C 0.7728(13) 0.1362(10) 0.5891(14) 0.111(5) Uani 1 1 d . . .
H21A H 0.8437 0.1319 0.5633 0.133 Uiso 1 1 calc R . .
H21B H 0.7223 0.1448 0.5124 0.133 Uiso 1 1 calc R . .
C22 C 0.7462(10) 0.0605(7) 0.6607(12) 0.078(3) Uani 1 1 d . . .
H22B H 0.6901 0.0286 0.6106 0.093 Uiso 1 1 calc R . .
H22A H 0.8079 0.0241 0.6786 0.093 Uiso 1 1 calc R . .
N1 N 0.4552(4) 0.1267(3) 0.5736(5) 0.0258(14) Uani 1 1 d . A .
H1 H 0.5092 0.1382 0.5334 0.031 Uiso 1 1 calc R . .
N2 N 0.4656(5) 0.0904(3) 0.6946(5) 0.0256(14) Uani 1 1 d . . .
O1 O 0.4303(4) -0.0362(3) 0.6061(5) 0.0311(12) Uani 1 1 d . . .
O2 O 0.5060(4) 0.2176(3) 0.7830(5) 0.0322(13) Uani 1 1 d . . .
O3 O 0.7369(5) -0.0669(4) 0.1312(5) 0.0538(17) Uani 1 1 d . . .
O4 O 0.7122(5) 0.0893(4) 0.7772(8) 0.071(2) Uani 1 1 d . . .
F1' F -0.0071(11) 0.1275(10) 0.3047(18) 0.092(4) Uani 0.537(12) 1 d P A 1
F1 F 0.0284(13) 0.1747(15) 0.221(2) 0.092(4) Uani 0.463(12) 1 d P A 2
F2 F 0.0398(9) 0.2829(10) 0.2964(16) 0.100(5) Uani 0.597(14) 1 d P A 1
F2' F 0.0444(15) 0.2251(19) 0.230(3) 0.100(5) Uani 0.403(14) 1 d P A 2
F3 F -0.0209(7) 0.2227(11) 0.4181(10) 0.097(5) Uani 0.746(19) 1 d P A 1
F3' F -0.023(3) 0.164(4) 0.376(4) 0.097(5) Uani 0.254(19) 1 d P A 2

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
C1 0.066(7) 0.082(8) 0.032(5) 0.013(6) -0.007(5) -0.003(6)
C2 0.049(5) 0.041(5) 0.052(6) -0.004(4) 0.005(4) 0.003(4)
C3 0.046(5) 0.046(5) 0.036(5) 0.005(4) 0.014(4) 0.001(4)
C4 0.052(5) 0.029(4) 0.020(4) -0.001(3) 0.011(3) 0.002(3)
C5 0.046(4) 0.012(3) 0.027(4) -0.001(3) 0.006(3) 0.001(3)
C6 0.047(5) 0.030(4) 0.024(4) 0.010(3) 0.010(3) -0.002(3)
C7 0.056(5) 0.033(4) 0.021(4) 0.006(3) 0.004(3) -0.005(4)
C8 0.035(4) 0.010(3) 0.028(4) -0.005(3) 0.008(3) 0.003(3)
C9 0.034(4) 0.013(3) 0.034(4) -0.002(3) 0.008(3) 0.006(3)
C10 0.030(3) 0.011(3) 0.025(4) 0.002(3) 0.011(3) 0.004(3)
C11 0.036(4) 0.010(3) 0.024(4) 0.008(3) 0.011(3) 0.005(3)
C12 0.038(4) 0.012(4) 0.027(4) -0.005(3) 0.006(3) 0.005(3)
C13 0.048(4) 0.011(3) 0.021(4) 0.004(3) 0.000(3) -0.001(3)
C14 0.035(4) 0.014(3) 0.031(4) -0.001(3) 0.003(3) -0.002(3)
C15 0.061(7) 0.070(8) 0.117(11) -0.012(8) 0.031(7) -0.013(6)
C16 0.182(19) 0.26(3) 0.122(14) -0.090(16) 0.071(14) -0.160(19)
C17 0.073(8) 0.167(14) 0.050(7) -0.014(8) 0.024(6) -0.025(8)
C18 0.061(6) 0.064(6) 0.032(5) 0.002(5) 0.015(4) -0.004(5)
C19 0.058(7) 0.082(9) 0.131(13) -0.052(9) 0.003(7) -0.015(6)
C20 0.078(8) 0.059(8) 0.131(13) -0.005(9) -0.038(8) 0.005(6)
C21 0.134(13) 0.111(12) 0.089(10) -0.018(10) 0.024(9) -0.045(10)
C22 0.088(8) 0.057(7) 0.083(9) -0.015(7) -0.006(7) -0.007(6)
N1 0.035(3) 0.023(3) 0.020(3) 0.008(3) 0.007(2) -0.001(2)
N2 0.040(3) 0.012(3) 0.025(3) 0.005(2) 0.005(3) 0.002(2)
O1 0.050(3) 0.016(2) 0.028(3) 0.001(2) 0.004(2) 0.002(2)
O2 0.060(3) 0.014(3) 0.024(3) 0.005(2) 0.008(2) -0.002(2)
O3 0.058(4) 0.071(4) 0.034(3) 0.011(3) 0.010(3) -0.007(3)
O4 0.059(4) 0.063(5) 0.090(6) -0.025(4) 0.009(4) -0.014(3)
F1' 0.063(7) 0.105(11) 0.103(10) -0.030(8) -0.018(6) -0.009(6)
F1 0.063(7) 0.105(11) 0.103(10) -0.030(8) -0.018(6) -0.009(6)
F2 0.063(5) 0.082(9) 0.150(14) 0.064(9) -0.013(7) 0.010(7)
F2' 0.063(5) 0.082(9) 0.150(14) 0.064(9) -0.013(7) 0.010(7)
F3 0.060(5) 0.178(14) 0.053(6) 0.006(7) 0.007(4) 0.049(7)
F3' 0.060(5) 0.178(14) 0.053(6) 0.006(7) 0.007(4) 0.049(7)

_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
C1 F3' 1.18(4) . ?
C1 F2' 1.24(3) . ?
C1 F3 1.314(16) . ?
C1 F1 1.34(2) . ?
C1 F2 1.406(18) . ?
C1 F1' 1.405(18) . ?
C1 C2 1.479(13) . ?
C2 C3 1.364(12) . ?
C2 C7 1.394(12) . ?
C3 C4 1.381(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(10) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(10) . ?
C5 N1 1.426(9) . ?
C6 C7 1.375(11) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 O1 1.212(8) . ?
C8 N2 1.394(8) . ?
C8 C9 1.486(10) . ?
C9 C14 1.385(9) . ?
C9 C10 1.398(10) . ?
C10 C11 1.423(9) . ?
C10 C10 1.426(13) 3_657 ?
C11 C13 1.367(10) . ?
C11 C12 1.505(9) . ?
C12 O2 1.209(8) . ?
C12 N2 1.412(9) . ?
C13 C14 1.405(10) 3_657 ?
C13 H13 0.9500 . ?
C14 C13 1.405(10) 3_657 ?
C14 H14 0.9500 . ?
C15 C16 1.376(19) . ?
C15 O3 1.398(12) . ?
C15 H15B 0.9900 . ?
C15 H15A 0.9900 . ?
C16 C17 1.47(2) . ?
C16 H16B 0.9900 . ?
C16 H16A 0.9900 . ?
C17 C18 1.462(14) . ?
C17 H17B 0.9900 . ?
C17 H17A 0.9900 . ?
C18 O3 1.437(10) . ?
C18 H18B 0.9900 . ?
C18 H18A 0.9900 . ?
C19 O4 1.390(13) . ?
C19 C20 1.466(19) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.493(18) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.496(18) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 O4 1.433(14) . ?
C22 H22B 0.9900 . ?
C22 H22A 0.9900 . ?
N1 N2 1.400(8) . ?
N1 H1 0.8800 . ?
F1 F2' 0.84(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
F3' C1 F2' 121(2) . . ?
F3' C1 F3 49(3) . . ?
F2' C1 F3 123.4(16) . . ?
F3' C1 F1 94(3) . . ?
F3 C1 F1 127.4(12) . . ?
F3' C1 F2 124(3) . . ?
F2' C1 F2 52.0(17) . . ?
F3 C1 F2 86.1(12) . . ?
F1 C1 F2 88.3(14) . . ?
F2' C1 F1' 92.2(18) . . ?
F3 C1 F1' 92.6(12) . . ?
F1 C1 F1' 55.9(12) . . ?
F2 C1 F1' 132.7(11) . . ?
F3' C1 C2 118.1(18) . . ?
F2' C1 C2 113.8(13) . . ?
F3 C1 C2 116.8(9) . . ?
F1 C1 C2 113.8(11) . . ?
F2 C1 C2 111.9(10) . . ?
F1' C1 C2 110.7(10) . . ?
C3 C2 C7 119.4(8) . . ?
C3 C2 C1 119.8(8) . . ?
C7 C2 C1 120.8(9) . . ?
C2 C3 C4 122.0(8) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 118.8(7) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 119.7(7) . . ?
C4 C5 N1 123.3(6) . . ?
C6 C5 N1 116.9(6) . . ?
C7 C6 C5 120.5(7) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C2 119.5(7) . . ?
C6 C7 H7 120.2 . . ?
C2 C7 H7 120.2 . . ?
O1 C8 N2 120.5(6) . . ?
O1 C8 C9 123.3(6) . . ?
N2 C8 C9 116.2(6) . . ?
C14 C9 C10 120.8(7) . . ?
C14 C9 C8 118.7(6) . . ?
C10 C9 C8 120.5(6) . . ?
C9 C10 C11 122.7(6) . . ?
C9 C10 C10 119.8(7) . 3_657 ?
C11 C10 C10 117.5(8) . 3_657 ?
C13 C11 C10 121.9(6) . . ?
C13 C11 C12 120.4(6) . . ?
C10 C11 C12 117.7(6) . . ?
O2 C12 N2 121.1(6) . . ?
O2 C12 C11 121.7(6) . . ?
N2 C12 C11 117.2(6) . . ?
C11 C13 C14 119.7(6) . 3_657 ?
C11 C13 H13 120.1 . . ?
C14 C13 H13 120.1 3_657 . ?
C9 C14 C13 120.2(7) . 3_657 ?
C9 C14 H14 119.9 . . ?
C13 C14 H14 119.9 3_657 . ?
C16 C15 O3 107.9(11) . . ?
C16 C15 H15B 110.1 . . ?
O3 C15 H15B 110.1 . . ?
C16 C15 H15A 110.1 . . ?
O3 C15 H15A 110.1 . . ?
H15B C15 H15A 108.4 . . ?
C15 C16 C17 110.3(12) . . ?
C15 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
C15 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
H16B C16 H16A 108.1 . . ?
C16 C17 C18 102.7(10) . . ?
C16 C17 H17B 111.2 . . ?
C18 C17 H17B 111.2 . . ?
C16 C17 H17A 111.2 . . ?
C18 C17 H17A 111.2 . . ?
H17B C17 H17A 109.1 . . ?
O3 C18 C17 107.0(8) . . ?
O3 C18 H18B 110.3 . . ?
C17 C18 H18B 110.3 . . ?
O3 C18 H18A 110.3 . . ?
C17 C18 H18A 110.3 . . ?
H18B C18 H18A 108.6 . . ?
O4 C19 C20 104.9(11) . . ?
O4 C19 H19A 110.8 . . ?
C20 C19 H19A 110.8 . . ?
O4 C19 H19B 110.8 . . ?
C20 C19 H19B 110.8 . . ?
H19A C19 H19B 108.8 . . ?
C19 C20 C21 105.1(11) . . ?
C19 C20 H20A 110.7 . . ?
C21 C20 H20A 110.7 . . ?
C19 C20 H20B 110.7 . . ?
C21 C20 H20B 110.7 . . ?
H20A C20 H20B 108.8 . . ?
C20 C21 C22 103.5(11) . . ?
C20 C21 H21A 111.1 . . ?
C22 C21 H21A 111.1 . . ?
C20 C21 H21B 111.1 . . ?
C22 C21 H21B 111.1 . . ?
H21A C21 H21B 109.0 . . ?
O4 C22 C21 106.5(10) . . ?
O4 C22 H22B 110.4 . . ?
C21 C22 H22B 110.4 . . ?
O4 C22 H22A 110.4 . . ?
C21 C22 H22A 110.4 . . ?
H22B C22 H22A 108.6 . . ?
N2 N1 C5 115.5(5) . . ?
N2 N1 H1 122.2 . . ?
C5 N1 H1 122.2 . . ?
C8 N2 N1 117.6(6) . . ?
C8 N2 C12 125.7(6) . . ?
N1 N2 C12 116.6(5) . . ?
C15 O3 C18 106.5(8) . . ?
C19 O4 C22 105.9(9) . . ?
F2' F1 C1 65(3) . . ?
F1 F2' C1 77(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
F3' C1 C2 C3 -37(4) . . . . ?
F2' C1 C2 C3 172(2) . . . . ?
F3 C1 C2 C3 18.7(17) . . . . ?
F1 C1 C2 C3 -146.3(16) . . . . ?
F2 C1 C2 C3 115.6(12) . . . . ?
F1' C1 C2 C3 -85.4(14) . . . . ?
F3' C1 C2 C7 143(4) . . . . ?
F2' C1 C2 C7 -7(3) . . . . ?
F3 C1 C2 C7 -161.0(12) . . . . ?
F1 C1 C2 C7 34(2) . . . . ?
F2 C1 C2 C7 -64.1(14) . . . . ?
F1' C1 C2 C7 94.8(14) . . . . ?
C7 C2 C3 C4 0.0(13) . . . . ?
C1 C2 C3 C4 -179.7(9) . . . . ?
C2 C3 C4 C5 -0.8(12) . . . . ?
C3 C4 C5 C6 0.9(11) . . . . ?
C3 C4 C5 N1 179.1(7) . . . . ?
C4 C5 C6 C7 -0.3(11) . . . . ?
N1 C5 C6 C7 -178.6(7) . . . . ?
C5 C6 C7 C2 -0.5(12) . . . . ?
C3 C2 C7 C6 0.6(13) . . . . ?
C1 C2 C7 C6 -179.7(9) . . . . ?
O1 C8 C9 C14 -1.1(10) . . . . ?
N2 C8 C9 C14 179.3(6) . . . . ?
O1 C8 C9 C10 -179.9(6) . . . . ?
N2 C8 C9 C10 0.5(9) . . . . ?
C14 C9 C10 C11 -179.7(7) . . . . ?
C8 C9 C10 C11 -0.9(10) . . . . ?
C14 C9 C10 C10 -0.2(11) . . . 3_657 ?
C8 C9 C10 C10 178.5(7) . . . 3_657 ?
C9 C10 C11 C13 178.5(7) . . . . ?
C10 C10 C11 C13 -1.0(11) 3_657 . . . ?
C9 C10 C11 C12 -0.6(9) . . . . ?
C10 C10 C11 C12 179.9(7) 3_657 . . . ?
C13 C11 C12 O2 1.8(10) . . . . ?
C10 C11 C12 O2 -179.1(6) . . . . ?
C13 C11 C12 N2 -176.7(6) . . . . ?
C10 C11 C12 N2 2.5(9) . . . . ?
C10 C11 C13 C14 2.7(10) . . . 3_657 ?
C12 C11 C13 C14 -178.2(6) . . . 3_657 ?
C10 C9 C14 C13 -1.5(10) . . . 3_657 ?
C8 C9 C14 C13 179.7(6) . . . 3_657 ?
O3 C15 C16 C17 11(2) . . . . ?
C15 C16 C17 C18 3(2) . . . . ?
C16 C17 C18 O3 -16.6(17) . . . . ?
O4 C19 C20 C21 -32.6(14) . . . . ?
C19 C20 C21 C22 14.1(15) . . . . ?
C20 C21 C22 O4 8.4(14) . . . . ?
C4 C5 N1 N2 15.6(9) . . . . ?
C6 C5 N1 N2 -166.2(6) . . . . ?
O1 C8 N2 N1 -1.9(9) . . . . ?
C9 C8 N2 N1 177.7(5) . . . . ?
O1 C8 N2 C12 -178.0(6) . . . . ?
C9 C8 N2 C12 1.5(9) . . . . ?
C5 N1 N2 C8 82.6(7) . . . . ?
C5 N1 N2 C12 -100.8(7) . . . . ?
O2 C12 N2 C8 178.5(7) . . . . ?
C11 C12 N2 C8 -3.0(9) . . . . ?
O2 C12 N2 N1 2.3(9) . . . . ?
C11 C12 N2 N1 -179.2(6) . . . . ?
C16 C15 O3 C18 -22.0(17) . . . . ?
C17 C18 O3 C15 24.2(12) . . . . ?
C20 C19 O4 C22 38.4(12) . . . . ?
C21 C22 O4 C19 -29.3(13) . . . . ?
F3' C1 F1 F2' 138(3) . . . . ?
F3 C1 F1 F2' 98(3) . . . . ?
F2 C1 F1 F2' 15(2) . . . . ?
F1' C1 F1 F2' 162(2) . . . . ?
C2 C1 F1 F2' -99(2) . . . . ?
F3' C1 F2' F1 -51(4) . . . . ?
F3 C1 F2' F1 -110(3) . . . . ?
F2 C1 F2' F1 -161(3) . . . . ?
F1' C1 F2' F1 -15(2) . . . . ?
C2 C1 F2' F1 99(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        25.46
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.109
_database_code_depnum_ccdc_archive 'CCDC 936251'