# Electronic Supplementary Material (ESI) for ChemComm.
# 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_AZUL_4_1_ss413

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 1,3,5,7-tetra(trifluoromethyl)azulene
;
_chemical_name_common            azulene-4-1
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H4 F12'
_chemical_formula_sum            'C14 H4 F12'
_chemical_formula_weight         400.17

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'

_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                   8.9064(4)
_cell_length_b                   9.5245(4)
_cell_length_c                   13.4137(6)
_cell_angle_alpha                105.240(2)
_cell_angle_beta                 101.204(2)
_cell_angle_gamma                101.091(2)
_cell_volume                     1040.70(8)
_cell_formula_units_Z            3
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9937
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      28.25

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.916
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             588
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9521
_exptl_absorpt_correction_T_max  0.9822
_exptl_absorpt_process_details   'SCALE (Bruker, 2009)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(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            22507
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         28.31
_reflns_number_total             5131
_reflns_number_gt                3999
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2009)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0516P)²+1.0732P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5131
_refine_ls_number_parameters     385
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1283
_refine_ls_wR_factor_gt          0.1173
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.66696(18) 0.19899(15) -0.08628(11) 0.0391(3) Uani 1 1 d . . .
F2 F 0.5250(2) 0.3527(2) -0.10792(14) 0.0640(6) Uani 1 1 d . . .
F3 F 0.73070(19) 0.42037(16) 0.02275(12) 0.0453(4) Uani 1 1 d . . .
F4 F 0.05356(17) 0.2739(2) -0.05454(11) 0.0460(4) Uani 1 1 d . . .
F5 F -0.03523(16) 0.14816(18) 0.04133(14) 0.0475(4) Uani 1 1 d . . .
F6 F 0.07462(19) 0.38230(19) 0.10983(13) 0.0552(5) Uani 1 1 d . . .
F7 F 0.14349(15) -0.07007(15) 0.27888(10) 0.0345(3) Uani 1 1 d . . .
F8 F 0.21640(15) 0.15479(15) 0.38822(11) 0.0329(3) Uani 1 1 d . . .
F9 F 0.31592(16) -0.01815(17) 0.42852(11) 0.0382(3) Uani 1 1 d . . .
F10 F 0.87116(16) 0.06671(19) 0.36399(12) 0.0453(4) Uani 1 1 d . . .
F11 F 0.90554(14) 0.23008(14) 0.28111(11) 0.0321(3) Uani 1 1 d . . .
F12 F 0.83332(15) -0.00454(15) 0.19345(12) 0.0375(3) Uani 1 1 d . . .
C1 C 0.5095(2) 0.2504(2) 0.03430(16) 0.0213(4) Uani 1 1 d . . .
C2 C 0.3542(2) 0.2617(2) 0.01864(16) 0.0227(4) Uani 1 1 d . . .
H2 H 0.3186 0.3002 -0.0377 0.027 Uiso 1 1 calc R . .
C3 C 0.2433(2) 0.2247(2) 0.07385(15) 0.0210(4) Uani 1 1 d . . .
C4 C 0.2601(2) 0.1656(2) 0.16041(16) 0.0228(4) Uani 1 1 d . . .
H4 H 0.1691 0.1475 0.1868 0.027 Uiso 1 1 calc R . .
C5 C 0.3913(2) 0.1307(2) 0.21167(16) 0.0214(4) Uani 1 1 d . . .
C6 C 0.3997(2) 0.0730(2) 0.29730(15) 0.0212(4) Uani 1 1 d . . .
C7 C 0.5523(2) 0.0540(2) 0.32920(16) 0.0245(4) Uani 1 1 d . . .
H7 H 0.5880 0.0158 0.3856 0.029 Uiso 1 1 calc R . .
C8 C 0.6431(2) 0.1008(2) 0.26403(16) 0.0221(4) Uani 1 1 d . . .
C9 C 0.5500(2) 0.1476(2) 0.18898(16) 0.0216(4) Uani 1 1 d . . .
C10 C 0.5977(2) 0.1994(2) 0.11061(16) 0.0235(4) Uani 1 1 d . . .
H10 H 0.7036 0.2010 0.1074 0.028 Uiso 1 1 calc R . .
C11 C 0.6054(2) 0.3047(2) -0.03619(17) 0.0251(4) Uani 1 1 d . . .
C12 C 0.0841(2) 0.2569(2) 0.04131(16) 0.0234(4) Uani 1 1 d . . .
C13 C 0.2700(2) 0.0352(2) 0.34823(16) 0.0231(4) Uani 1 1 d . . .
C14 C 0.8117(2) 0.0983(2) 0.27638(16) 0.0237(4) Uani 1 1 d . . .
C15 C 0.3270(2) 0.5874(2) 0.38377(16) 0.0216(4) Uani 1 1 d . A -1
C16 C -0.2268(2) 0.6399(2) 0.31109(16) 0.0221(4) Uani 1 1 d . A -1
F13 F 0.3368(2) 0.6444(2) 0.30532(13) 0.0570(5) Uani 1 1 d . A -1
F14 F 0.36512(18) 0.45625(16) 0.35695(13) 0.0455(4) Uani 1 1 d . A -1
F15 F 0.44190(16) 0.67689(18) 0.46861(11) 0.0464(4) Uani 1 1 d . A -1
F16 F -0.27271(18) 0.74856(16) 0.37318(11) 0.0413(4) Uani 1 1 d . A -1
F17 F -0.35646(15) 0.52472(15) 0.26484(11) 0.0366(3) Uani 1 1 d . A -1
F18 F -0.1884(2) 0.6888(2) 0.23326(12) 0.0573(5) Uani 1 1 d . A -1
C27 C 0.0530(5) 0.6234(5) 0.3292(4) 0.0175(9) Uani 0.50 1 d PD A -1
H27 H 0.0697 0.6634 0.2732 0.021 Uiso 0.50 1 calc PR A -1
C25 C 0.1676(5) 0.4673(5) 0.5424(4) 0.0181(8) Uani 0.50 1 d PD A -1
H25 H 0.2747 0.4659 0.5450 0.022 Uiso 0.50 1 calc PR A -1
C22 C 0.0960(5) 0.5246(4) 0.4665(3) 0.0166(7) Uani 0.50 1 d PD A -1
C24 C -0.1848(5) 0.5014(5) 0.4958(4) 0.0178(8) Uani 0.50 1 d PD A -1
H24 H -0.2845 0.5197 0.4716 0.021 Uiso 0.50 1 calc PR A -1
C23 C -0.0700(5) 0.5407(4) 0.4449(3) 0.0173(7) Uani 0.50 1 d PD A -1
C17 C -0.0879(6) 0.6013(6) 0.3606(4) 0.0212(4) Uani 0.50 1 d PD A -1
C18 C 0.1667(15) 0.5774(14) 0.3931(8) 0.0202(17) Uani 0.50 1 d PD A -1
C26A C -0.0464(6) 0.3990(5) 0.6320(4) 0.0192(10) Uani 0.50 1 d P A -1
H26A H -0.0653 0.3584 0.6873 0.023 Uiso 0.50 1 calc PR A -1
C17A C 0.1040(6) 0.4110(5) 0.6159(4) 0.0213(4) Uani 0.50 1 d PD A -1
C18A C -0.1709(13) 0.4378(13) 0.5788(7) 0.0168(15) Uani 0.50 1 d PD A -1


_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 C11 1.329(2) . ?
F2 C11 1.317(2) . ?
F3 C11 1.345(3) . ?
F4 C12 1.320(2) . ?
F5 C12 1.334(2) . ?
F6 C12 1.330(3) . ?
F7 C13 1.345(2) . ?
F8 C13 1.342(2) . ?
F9 C13 1.335(2) . ?
F10 C14 1.326(2) . ?
F11 C14 1.346(2) . ?
F12 C14 1.348(2) . ?
C1 C2 1.388(3) . ?
C1 C10 1.413(3) . ?
C1 C11 1.514(3) . ?
C2 C3 1.391(3) . ?
C3 C4 1.413(3) . ?
C3 C12 1.514(3) . ?
C4 C5 1.381(3) . ?
C5 C6 1.393(3) . ?
C5 C9 1.490(3) . ?
C6 C7 1.404(3) . ?
C6 C13 1.486(3) . ?
C7 C8 1.399(3) . ?
C8 C9 1.398(3) . ?
C8 C14 1.484(3) . ?
C9 C10 1.376(3) . ?
C15 F13 1.314(2) . ?
C15 F15 1.331(2) . ?
C15 F14 1.334(2) . ?
C15 C18 1.445(13) . ?
C16 F18 1.326(2) . ?
C16 F16 1.332(2) . ?
C16 F17 1.341(2) . ?
C16 C17 1.446(6) . ?
C27 C17 1.396(6) . ?
C27 C18 1.408(11) . ?
C25 C22 1.384(6) . ?
C25 C17A 1.399(6) . ?
C22 C18 1.414(8) . ?
C22 C23 1.496(5) . ?
C24 C23 1.382(6) . ?
C24 C18A 1.398(8) . ?
C23 C17 1.394(5) . ?
C26A C18A 1.365(11) . ?
C26A C17A 1.386(7) . ?

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
C2 C1 C10 129.57(18) . . ?
C2 C1 C11 117.51(18) . . ?
C10 C1 C11 112.88(17) . . ?
C1 C2 C3 129.08(19) . . ?
C2 C3 C4 128.83(18) . . ?
C2 C3 C12 116.85(18) . . ?
C4 C3 C12 114.28(17) . . ?
C5 C4 C3 128.57(19) . . ?
C4 C5 C6 125.52(19) . . ?
C4 C5 C9 128.00(18) . . ?
C6 C5 C9 106.48(17) . . ?
C5 C6 C7 109.27(18) . . ?
C5 C6 C13 126.59(18) . . ?
C7 C6 C13 124.14(18) . . ?
C8 C7 C6 108.64(18) . . ?
C9 C8 C7 109.34(17) . . ?
C9 C8 C14 127.42(18) . . ?
C7 C8 C14 123.24(18) . . ?
C10 C9 C8 126.15(19) . . ?
C10 C9 C5 127.59(18) . . ?
C8 C9 C5 106.26(17) . . ?
C9 C10 C1 128.35(19) . . ?
F2 C11 F1 108.58(18) . . ?
F2 C11 F3 106.41(18) . . ?
F1 C11 F3 105.01(17) . . ?
F2 C11 C1 113.74(17) . . ?
F1 C11 C1 111.77(17) . . ?
F3 C11 C1 110.82(17) . . ?
F4 C12 F6 106.83(18) . . ?
F4 C12 F5 107.04(17) . . ?
F6 C12 F5 105.70(18) . . ?
F4 C12 C3 113.62(16) . . ?
F6 C12 C3 111.07(17) . . ?
F5 C12 C3 112.11(17) . . ?
F9 C13 F8 107.07(16) . . ?
F9 C13 F7 106.68(16) . . ?
F8 C13 F7 105.99(16) . . ?
F9 C13 C6 111.97(17) . . ?
F8 C13 C6 112.37(17) . . ?
F7 C13 C6 112.34(16) . . ?
F10 C14 F11 106.96(17) . . ?
F10 C14 F12 106.73(17) . . ?
F11 C14 F12 104.91(16) . . ?
F10 C14 C8 112.30(17) . . ?
F11 C14 C8 112.91(17) . . ?
F12 C14 C8 112.50(17) . . ?
F13 C15 F15 106.73(18) . . ?
F13 C15 F14 106.70(17) . . ?
F15 C15 F14 105.90(17) . . ?
F13 C15 C18 105.1(3) . . ?
F15 C15 C18 116.4(5) . . ?
F14 C15 C18 115.3(5) . . ?
F18 C16 F16 106.92(17) . . ?
F18 C16 F17 106.37(17) . . ?
F16 C16 F17 105.90(16) . . ?
F18 C16 C17 105.3(2) . . ?
F16 C16 C17 116.4(2) . . ?
F17 C16 C17 115.3(2) . . ?
C17 C27 C18 109.6(6) . . ?
C22 C25 C17A 128.9(4) . . ?
C25 C22 C18 126.0(6) . . ?
C25 C22 C23 127.2(4) . . ?
C18 C22 C23 106.8(6) . . ?
C23 C24 C18A 127.4(6) . . ?
C24 C23 C17 126.3(4) . . ?
C24 C23 C22 127.6(4) . . ?
C17 C23 C22 106.1(4) . . ?
C23 C17 C27 109.6(4) . . ?
C23 C17 C16 127.5(4) . . ?
C27 C17 C16 122.9(4) . . ?
C27 C18 C22 107.8(9) . . ?
C27 C18 C15 124.4(5) . . ?
C22 C18 C15 127.7(7) . . ?
C18A C26A C17A 128.5(5) . . ?
C26A C17A C25 129.1(5) . . ?
C26A C18A C24 131.2(7) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.829
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 980904'
#######################################################################
#
#                 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_azul_4_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 1,2,3,5-tetra(trifluoromethyl)azulene 
;
_chemical_name_common            AZUL-4-2
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H4 F12'
_chemical_formula_sum            'C14 H4 F12'
_chemical_formula_weight         400.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0020 0.0005 '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 -0.0050 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

_cell_length_a                   4.8939(3)
_cell_length_b                   32.3450(18)
_cell_length_c                   8.6013(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.4396(11)
_cell_angle_gamma                90.00
_cell_volume                     1357.44(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9918
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      22.76

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.958
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.41328
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17319
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -52
_diffrn_reflns_limit_k_max       53
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         0.73
_diffrn_reflns_theta_max         20.13
_reflns_number_total             4394
_reflns_number_gt                3995
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2009)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0730P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.1(13)
_refine_ls_number_reflns         4394
_refine_ls_number_parameters     263
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.0963
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_restrained_S_all      1.194
_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 0.2764(3) 0.17969(4) 0.13062(17) 0.0129(2) Uani 1 1 d . . .
C2 C 0.3233(3) 0.15515(5) 0.00052(17) 0.0134(2) Uani 1 1 d . . .
C3 C 0.2123(3) 0.11543(5) 0.01929(18) 0.0151(3) Uani 1 1 d . . .
C4 C -0.0764(4) 0.08228(5) 0.21413(19) 0.0174(3) Uani 1 1 d . . .
H4 H -0.0818 0.0579 0.1523 0.021 Uiso 1 1 calc R . .
C5 C -0.2204(4) 0.08039(5) 0.3480(2) 0.0189(3) Uani 1 1 d . A .
C6 C -0.2567(4) 0.11106(5) 0.4593(2) 0.0209(3) Uani 1 1 d . . .
H6 H -0.3637 0.1033 0.5420 0.025 Uiso 1 1 calc R . .
C7 C -0.1578(4) 0.15132(6) 0.4655(2) 0.0213(3) Uani 1 1 d . . .
H7 H -0.2109 0.1674 0.5506 0.026 Uiso 1 1 calc R . .
C8 C 0.0082(4) 0.17159(5) 0.36485(18) 0.0169(3) Uani 1 1 d . . .
H8 H 0.0537 0.1994 0.3916 0.020 Uiso 1 1 calc R . .
C9 C 0.1168(3) 0.15662(4) 0.23007(17) 0.0130(2) Uani 1 1 d . . .
C10 C 0.0750(3) 0.11520(4) 0.15856(18) 0.0140(2) Uani 1 1 d . . .
C11 C 0.3856(3) 0.22257(5) 0.16101(18) 0.0154(3) Uani 1 1 d . . .
C12 C 0.4494(3) 0.17083(5) -0.14348(19) 0.0169(3) Uani 1 1 d . . .
C13 C 0.2444(5) 0.07943(6) -0.0888(2) 0.0241(4) Uani 1 1 d . . .
C14 C -0.3533(5) 0.03910(6) 0.3803(2) 0.0269(4) Uani 1 1 d . . .
F1 F 0.4202(3) 0.23115(3) 0.31428(13) 0.0233(2) Uani 1 1 d . . .
F2 F 0.2213(3) 0.25233(3) 0.09673(14) 0.0207(2) Uani 1 1 d . . .
F3 F 0.6324(2) 0.22769(4) 0.10495(15) 0.0232(2) Uani 1 1 d . . .
F4 F 0.3906(3) 0.21081(4) -0.16882(14) 0.0241(2) Uani 1 1 d . . .
F5 F 0.7222(2) 0.16689(4) -0.13519(14) 0.0237(2) Uani 1 1 d . . .
F6 F 0.3503(3) 0.15061(4) -0.27257(13) 0.0265(2) Uani 1 1 d . . .
F7 F 0.4945(3) 0.07947(4) -0.14338(17) 0.0316(3) Uani 1 1 d . . .
F8 F 0.0615(3) 0.07975(5) -0.21372(17) 0.0367(3) Uani 1 1 d . . .
F9 F 0.2204(4) 0.04310(4) -0.0184(2) 0.0477(5) Uani 1 1 d . . .
F10 F -0.5689(16) 0.04312(19) 0.4755(7) 0.0426(17) Uani 0.449(9) 1 d P A 1
F10B F -0.5983(10) 0.04229(19) 0.4080(12) 0.068(2) Uani 0.551(9) 1 d P A 2
F11 F -0.1978(9) 0.01231(15) 0.4335(12) 0.053(2) Uani 0.449(9) 1 d P A 1
F11B F -0.2155(9) 0.02208(12) 0.5122(5) 0.0381(9) Uani 0.551(9) 1 d P A 2
F12 F -0.4989(12) 0.02488(13) 0.2469(4) 0.0381(14) Uani 0.449(9) 1 d P A 1
F12B F -0.3137(15) 0.00997(12) 0.2726(4) 0.059(2) Uani 0.551(9) 1 d P A 2


_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 C2 1.405(2) . ?
C1 C9 1.415(2) . ?
C1 C11 1.502(2) . ?
C2 C3 1.409(2) . ?
C2 C12 1.514(2) . ?
C3 C10 1.418(2) . ?
C3 C13 1.506(2) . ?
C4 C5 1.397(2) . ?
C4 C10 1.402(2) . ?
C5 C6 1.399(3) . ?
C5 C14 1.521(2) . ?
C6 C7 1.389(3) . ?
C7 C8 1.396(2) . ?
C8 C9 1.399(2) . ?
C9 C10 1.482(2) . ?
C11 F3 1.3448(19) . ?
C11 F1 1.3451(19) . ?
C11 F2 1.345(2) . ?
C12 F5 1.337(2) . ?
C12 F4 1.339(2) . ?
C12 F6 1.346(2) . ?
C13 F9 1.331(2) . ?
C13 F8 1.344(3) . ?
C13 F7 1.344(2) . ?
C14 F11 1.219(5) . ?
C14 F10B 1.245(6) . ?
C14 F12B 1.346(4) . ?
C14 F12 1.381(4) . ?
C14 F11B 1.388(4) . ?
C14 F10 1.391(5) . ?

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
C2 C1 C9 108.37(13) . . ?
C2 C1 C11 125.62(13) . . ?
C9 C1 C11 125.98(13) . . ?
C1 C2 C3 109.61(12) . . ?
C1 C2 C12 124.37(14) . . ?
C3 C2 C12 125.77(14) . . ?
C2 C3 C10 108.28(13) . . ?
C2 C3 C13 125.08(14) . . ?
C10 C3 C13 126.61(14) . . ?
C5 C4 C10 128.87(15) . . ?
C4 C5 C6 129.18(15) . . ?
C4 C5 C14 116.03(16) . . ?
C6 C5 C14 114.78(15) . . ?
C7 C6 C5 128.97(15) . . ?
C6 C7 C8 129.35(16) . . ?
C7 C8 C9 128.92(15) . . ?
C8 C9 C1 125.54(14) . . ?
C8 C9 C10 127.44(13) . . ?
C1 C9 C10 106.92(13) . . ?
C4 C10 C3 126.11(14) . . ?
C4 C10 C9 127.21(14) . . ?
C3 C10 C9 106.66(13) . . ?
F3 C11 F1 106.11(14) . . ?
F3 C11 F2 106.82(12) . . ?
F1 C11 F2 106.32(13) . . ?
F3 C11 C1 111.64(13) . . ?
F1 C11 C1 112.17(12) . . ?
F2 C11 C1 113.32(14) . . ?
F5 C12 F4 107.57(15) . . ?
F5 C12 F6 106.98(13) . . ?
F4 C12 F6 106.01(14) . . ?
F5 C12 C2 113.14(13) . . ?
F4 C12 C2 111.14(12) . . ?
F6 C12 C2 111.61(14) . . ?
F9 C13 F8 107.06(18) . . ?
F9 C13 F7 105.93(17) . . ?
F8 C13 F7 106.78(16) . . ?
F9 C13 C3 112.62(15) . . ?
F8 C13 C3 113.12(17) . . ?
F7 C13 C3 110.88(16) . . ?
F11 C14 F10B 124.7(4) . . ?
F11 C14 F12B 69.0(5) . . ?
F10B C14 F12B 112.5(5) . . ?
F11 C14 F12 110.0(4) . . ?
F10B C14 F12 75.2(5) . . ?
F12B C14 F12 44.6(2) . . ?
F11 C14 F11B 33.0(4) . . ?
F10B C14 F11B 106.9(4) . . ?
F12B C14 F11B 101.4(3) . . ?
F12 C14 F11B 137.2(3) . . ?
F11 C14 F10 109.0(4) . . ?
F10B C14 F10 25.0(4) . . ?
F12B C14 F10 128.8(4) . . ?
F12 C14 F10 98.9(4) . . ?
F11B C14 F10 84.2(4) . . ?
F11 C14 C5 115.4(3) . . ?
F10B C14 C5 113.2(3) . . ?
F12B C14 C5 113.76(19) . . ?
F12 C14 C5 110.0(2) . . ?
F11B C14 C5 108.1(2) . . ?
F10 C14 C5 112.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.941
_diffrn_reflns_theta_full        20.13
_diffrn_measured_fraction_theta_full 0.941
_refine_diff_density_max         1.026
_refine_diff_density_min         -1.087
_refine_diff_density_rms         0.354
_database_code_depnum_ccdc_archive 'CCDC 980900'
#######################################################################
#
#                 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_AZUL-5-1-pyrene_ss406

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            AZUL-5-1-pyrene
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H3 F15, C16 H10'
_chemical_formula_sum            'C31 H13 F15'
_chemical_formula_weight         670.41

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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                   7.2226(7)
_cell_length_b                   16.1783(17)
_cell_length_c                   21.334(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.461(5)
_cell_angle_gamma                90.00
_cell_volume                     2490.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9715
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      30.58

_exptl_crystal_description       rod
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.788
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1336
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9062
_exptl_absorpt_correction_T_max  0.9592
_exptl_absorpt_process_details   'SCALE (Bruker, 2009)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(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            59030
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         30.58
_reflns_number_total             7578
_reflns_number_gt                6790
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2009)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0574P)²+1.3980P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7578
_refine_ls_number_parameters     425
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1095
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_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 0.72979(14) 0.84108(6) 0.90389(5) 0.01275(18) Uani 1 1 d . . .
C2 C 0.73857(14) 0.81507(6) 0.96677(5) 0.01295(18) Uani 1 1 d . . .
C3 C 0.71749(14) 0.72844(6) 0.96945(5) 0.01284(18) Uani 1 1 d . . .
C4 C 0.69121(15) 0.61440(6) 0.89020(5) 0.01440(18) Uani 1 1 d . . .
H4 H 0.6890 0.5763 0.9241 0.017 Uiso 1 1 calc R . .
C5 C 0.68034(15) 0.57933(6) 0.83062(5) 0.01460(19) Uani 1 1 d . A .
C6 C 0.68554(15) 0.61770(7) 0.77222(5) 0.01537(19) Uani 1 1 d . . .
H6 H 0.6769 0.5819 0.7369 0.018 Uiso 1 1 calc R . .
C7 C 0.70165(15) 0.70153(7) 0.75890(5) 0.01412(18) Uani 1 1 d . . .
C8 C 0.71338(14) 0.76907(6) 0.79987(5) 0.01378(18) Uani 1 1 d . . .
H8 H 0.7225 0.8217 0.7804 0.017 Uiso 1 1 calc R . .
C9 C 0.71356(14) 0.77001(6) 0.86515(5) 0.01192(17) Uani 1 1 d . . .
C10 C 0.70498(14) 0.69770(6) 0.90742(5) 0.01211(17) Uani 1 1 d . . .
C11 C 0.72396(15) 0.92940(7) 0.88209(5) 0.0167(2) Uani 1 1 d . . .
C12 C 0.77520(15) 0.87090(7) 1.02284(5) 0.0165(2) Uani 1 1 d . . .
C13 C 0.70436(15) 0.67795(7) 1.02810(5) 0.01618(19) Uani 1 1 d . . .
C14A C 0.66640(17) 0.48553(7) 0.82980(5) 0.0188(2) Uani 1 1 d . . .
F10A F 0.5601(3) 0.45702(8) 0.87348(7) 0.0533(5) Uani 0.874(3) 1 d P A 1
F11A F 0.82826(15) 0.44995(6) 0.83592(11) 0.0562(5) Uani 0.874(3) 1 d P A 1
F12A F 0.5885(3) 0.45673(6) 0.77581(5) 0.0426(4) Uani 0.874(3) 1 d P A 1
F10B F 0.703(2) 0.4518(5) 0.7803(5) 0.0533(5) Uani 0.126(3) 1 d P A 2
F11B F 0.5275(15) 0.4557(7) 0.8532(8) 0.0562(5) Uani 0.126(3) 1 d P A 2
F12B F 0.7944(16) 0.4527(5) 0.8751(4) 0.0426(4) Uani 0.126(3) 1 d P A 2
C15 C 0.70131(17) 0.72561(7) 0.69006(5) 0.0181(2) Uani 1 1 d . . .
C16 C 0.83335(17) 0.45633(7) 0.22129(6) 0.0220(2) Uani 1 1 d . . .
H16 H 0.8442 0.5148 0.2190 0.026 Uiso 1 1 calc R . .
C17 C 0.83059(18) 0.41792(8) 0.27954(6) 0.0223(2) Uani 1 1 d . . .
H17 H 0.8391 0.4504 0.3167 0.027 Uiso 1 1 calc R . .
C18 C 0.81552(16) 0.33244(7) 0.28398(5) 0.0190(2) Uani 1 1 d . . .
H18 H 0.8137 0.3070 0.3241 0.023 Uiso 1 1 calc R . .
C19 C 0.79152(16) 0.19476(7) 0.23270(5) 0.0192(2) Uani 1 1 d . . .
H19 H 0.7925 0.1682 0.2724 0.023 Uiso 1 1 calc R . .
C20 C 0.77933(17) 0.14850(7) 0.17984(6) 0.0202(2) Uani 1 1 d . . .
H20 H 0.7731 0.0900 0.1832 0.024 Uiso 1 1 calc R . .
C21 C 0.75888(16) 0.13893(8) 0.06361(6) 0.0218(2) Uani 1 1 d . . .
H21 H 0.7486 0.0805 0.0661 0.026 Uiso 1 1 calc R . .
C22 C 0.75716(16) 0.17740(9) 0.00530(6) 0.0250(3) Uani 1 1 d . . .
H22 H 0.7446 0.1449 -0.0318 0.030 Uiso 1 1 calc R . .
C23 C 0.77353(16) 0.26260(9) 0.00055(6) 0.0238(2) Uani 1 1 d . . .
H23 H 0.7730 0.2877 -0.0397 0.029 Uiso 1 1 calc R . .
C24 C 0.80813(17) 0.40057(8) 0.05188(6) 0.0234(2) Uani 1 1 d . . .
H24 H 0.8095 0.4271 0.0122 0.028 Uiso 1 1 calc R . .
C25 C 0.82249(17) 0.44700(8) 0.10466(6) 0.0228(2) Uani 1 1 d . . .
H25 H 0.8342 0.5053 0.1012 0.027 Uiso 1 1 calc R . .
C26 C 0.82037(15) 0.40976(7) 0.16590(5) 0.0174(2) Uani 1 1 d . . .
C27 C 0.80306(15) 0.28345(7) 0.22981(5) 0.01542(19) Uani 1 1 d . . .
C28 C 0.77563(15) 0.18591(7) 0.11872(5) 0.0167(2) Uani 1 1 d . . .
C29 C 0.79046(14) 0.27339(7) 0.11433(5) 0.01452(19) Uani 1 1 d . . .
C30 C 0.79079(15) 0.31210(8) 0.05450(5) 0.0186(2) Uani 1 1 d . . .
C31 C 0.80464(14) 0.32226(7) 0.17001(5) 0.01383(18) Uani 1 1 d . . .
F1 F 0.63670(12) 0.93733(5) 0.82532(4) 0.02635(17) Uani 1 1 d . . .
F2 F 0.89185(11) 0.96336(5) 0.87682(4) 0.02601(16) Uani 1 1 d . . .
F3 F 0.63127(11) 0.97785(4) 0.92067(4) 0.02545(16) Uani 1 1 d . . .
F4 F 0.87516(11) 0.93720(5) 1.00817(4) 0.02397(16) Uani 1 1 d . . .
F5 F 0.87169(10) 0.83181(5) 1.06889(3) 0.02226(15) Uani 1 1 d . . .
F6 F 0.61890(10) 0.89854(5) 1.04717(4) 0.02580(17) Uani 1 1 d . . .
F7 F 0.61877(11) 0.71855(5) 1.07315(3) 0.02355(16) Uani 1 1 d . . .
F8 F 0.87059(11) 0.65449(5) 1.05266(4) 0.02527(16) Uani 1 1 d . . .
F9 F 0.60695(11) 0.60786(5) 1.01805(3) 0.02317(16) Uani 1 1 d . . .
F13 F 0.71599(15) 0.66057(5) 0.65211(4) 0.0352(2) Uani 1 1 d . . .
F14 F 0.84011(10) 0.77720(5) 0.67797(3) 0.02306(15) Uani 1 1 d . . .
F15 F 0.54497(11) 0.76554(6) 0.67224(4) 0.02847(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
C1 C2 1.4047(14) . ?
C1 C9 1.4179(14) . ?
C1 C11 1.5028(15) . ?
C2 C3 1.4113(14) . ?
C2 C12 1.5130(14) . ?
C3 C10 1.4130(14) . ?
C3 C13 1.5005(14) . ?
C4 C5 1.3909(14) . ?
C4 C10 1.3993(14) . ?
C5 C6 1.3940(15) . ?
C5 C14A 1.5210(15) . ?
C6 C7 1.3915(15) . ?
C7 C8 1.3995(14) . ?
C7 C15 1.5193(15) . ?
C8 C9 1.3928(14) . ?
C9 C10 1.4801(14) . ?
C11 F3 1.3368(13) . ?
C11 F2 1.3403(13) . ?
C11 F1 1.3472(13) . ?
C12 F4 1.3374(13) . ?
C12 F5 1.3388(13) . ?
C12 F6 1.3395(13) . ?
C13 F7 1.3373(13) . ?
C13 F8 1.3439(13) . ?
C13 F9 1.3468(13) . ?
C14A F10B 1.227(8) . ?
C14A F11B 1.238(13) . ?
C14A F11A 1.3046(16) . ?
C14A F10A 1.3161(16) . ?
C14A F12A 1.3432(15) . ?
C14A F12B 1.412(9) . ?
C15 F13 1.3348(13) . ?
C15 F14 1.3381(14) . ?
C15 F15 1.3416(14) . ?
C16 C17 1.3903(18) . ?
C16 C26 1.4011(16) . ?
C17 C18 1.3908(17) . ?
C18 C27 1.4011(15) . ?
C19 C20 1.3532(17) . ?
C19 C27 1.4388(16) . ?
C20 C28 1.4367(16) . ?
C21 C22 1.3906(19) . ?
C21 C28 1.4008(15) . ?
C22 C23 1.388(2) . ?
C23 C30 1.4032(17) . ?
C24 C25 1.3539(19) . ?
C24 C30 1.4381(18) . ?
C25 C26 1.4394(16) . ?
C26 C31 1.4231(15) . ?
C27 C31 1.4224(14) . ?
C28 C29 1.4226(16) . ?
C29 C30 1.4220(15) . ?
C29 C31 1.4270(14) . ?

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
C2 C1 C9 108.24(9) . . ?
C2 C1 C11 125.44(9) . . ?
C9 C1 C11 126.16(9) . . ?
C1 C2 C3 109.61(9) . . ?
C1 C2 C12 125.12(9) . . ?
C3 C2 C12 125.19(9) . . ?
C2 C3 C10 108.32(9) . . ?
C2 C3 C13 125.82(9) . . ?
C10 C3 C13 125.84(9) . . ?
C5 C4 C10 129.30(10) . . ?
C4 C5 C6 129.23(10) . . ?
C4 C5 C14A 114.75(9) . . ?
C6 C5 C14A 115.99(9) . . ?
C7 C6 C5 128.48(10) . . ?
C6 C7 C8 129.55(10) . . ?
C6 C7 C15 116.79(9) . . ?
C8 C7 C15 113.63(9) . . ?
C9 C8 C7 129.08(10) . . ?
C8 C9 C1 126.04(9) . . ?
C8 C9 C10 127.04(9) . . ?
C1 C9 C10 106.88(9) . . ?
C4 C10 C3 125.87(9) . . ?
C4 C10 C9 127.28(9) . . ?
C3 C10 C9 106.84(9) . . ?
F3 C11 F2 106.87(9) . . ?
F3 C11 F1 105.68(9) . . ?
F2 C11 F1 105.99(9) . . ?
F3 C11 C1 112.03(9) . . ?
F2 C11 C1 113.72(9) . . ?
F1 C11 C1 112.00(9) . . ?
F4 C12 F5 106.34(9) . . ?
F4 C12 F6 107.18(9) . . ?
F5 C12 F6 107.11(9) . . ?
F4 C12 C2 111.82(9) . . ?
F5 C12 C2 111.47(9) . . ?
F6 C12 C2 112.58(9) . . ?
F7 C13 F8 106.93(9) . . ?
F7 C13 F9 105.88(9) . . ?
F8 C13 F9 106.03(9) . . ?
F7 C13 C3 112.30(9) . . ?
F8 C13 C3 113.05(9) . . ?
F9 C13 C3 112.14(9) . . ?
F10B C14A F11B 112.5(8) . . ?
F10B C14A F11A 70.3(8) . . ?
F11B C14A F11A 121.7(5) . . ?
F10B C14A F10A 127.4(4) . . ?
F11B C14A F10A 21.5(7) . . ?
F11A C14A F10A 108.78(14) . . ?
F10B C14A F12A 37.5(7) . . ?
F11B C14A F12A 83.9(7) . . ?
F11A C14A F12A 105.86(13) . . ?
F10A C14A F12A 104.47(12) . . ?
F10B C14A F12B 105.1(8) . . ?
F11B C14A F12B 95.5(7) . . ?
F11A C14A F12B 37.6(4) . . ?
F10A C14A F12B 76.6(5) . . ?
F12A C14A F12B 133.9(3) . . ?
F10B C14A C5 115.9(4) . . ?
F11B C14A C5 116.0(5) . . ?
F11A C14A C5 112.36(10) . . ?
F10A C14A C5 112.45(10) . . ?
F12A C14A C5 112.41(10) . . ?
F12B C14A C5 109.1(3) . . ?
F13 C15 F14 107.16(10) . . ?
F13 C15 F15 107.19(10) . . ?
F14 C15 F15 105.87(9) . . ?
F13 C15 C7 112.78(9) . . ?
F14 C15 C7 112.10(9) . . ?
F15 C15 C7 111.34(9) . . ?
C17 C16 C26 120.69(11) . . ?
C16 C17 C18 120.63(11) . . ?
C17 C18 C27 120.58(11) . . ?
C20 C19 C27 121.17(10) . . ?
C19 C20 C28 121.43(11) . . ?
C22 C21 C28 120.34(12) . . ?
C23 C22 C21 120.83(11) . . ?
C22 C23 C30 120.79(11) . . ?
C25 C24 C30 121.57(11) . . ?
C24 C25 C26 121.28(11) . . ?
C16 C26 C31 119.05(10) . . ?
C16 C26 C25 122.51(11) . . ?
C31 C26 C25 118.44(10) . . ?
C18 C27 C31 119.17(10) . . ?
C18 C27 C19 122.05(10) . . ?
C31 C27 C19 118.78(10) . . ?
C21 C28 C29 119.25(11) . . ?
C21 C28 C20 122.06(11) . . ?
C29 C28 C20 118.70(10) . . ?
C30 C29 C28 120.01(10) . . ?
C30 C29 C31 120.03(10) . . ?
C28 C29 C31 119.96(10) . . ?
C23 C30 C29 118.78(11) . . ?
C23 C30 C24 122.75(11) . . ?
C29 C30 C24 118.47(10) . . ?
C27 C31 C26 119.88(10) . . ?
C27 C31 C29 119.93(10) . . ?
C26 C31 C29 120.20(10) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        30.58
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.787
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 980901'
