# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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#  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.
#
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#  fide research purposes only. It may contain copyright material
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data_13S052
_audit_creation_date             2013-04-29
_audit_creation_method           
;
  Olex2 1.2-beta
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_chemical_formula_moiety         'C26 H24 F18 Li2 O2'
_chemical_formula_sum            'C26 H24 F18 Li2 O2'
_chemical_formula_weight         724.33
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Li -0.00003 0.00005 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   9.0486(5)
_cell_length_b                   12.7853(7)
_cell_length_c                   14.6892(8)
_cell_angle_alpha                84.024(2)
_cell_angle_beta                 74.906(2)
_cell_angle_gamma                69.739(2)
_cell_volume                     1539.05(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      2.47
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_correction_T_min  0.9201
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0636 before and 0.0417 after correction.
The Ratio of minimum to maximum transmission is 0.9264.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear orangish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.5629
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             728.7990
_exptl_crystal_preparation       'soaked in perfluoro polyether oil'
_exptl_crystal_size_max          0.441
_exptl_crystal_size_mid          0.335
_exptl_crystal_size_min          0.17
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            41365
_diffrn_reflns_theta_full        25.9998
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.47
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9993
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTON area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -10
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                5292
_reflns_number_total             6046
_reflns_threshold_expression     I>=2u(I)
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.9532
_refine_diff_density_min         -0.8762
_refine_diff_density_rms         0.1032
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             8.2397
_refine_ls_goodness_of_fit_ref   1.0614
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     436
_refine_ls_number_reflns         6046
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0495
_refine_ls_restrained_S_all      1.0614
_refine_ls_shift/su_max          0.0274
_refine_ls_shift/su_mean         0.0040
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0800P)²+1.2262P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1391
_refine_special_details          
'The CF3 group around C8 seems to be disordered as indicated by three Q-peaks around the carbon atom. Refinement of a disordered model, however, did not result in a physically meaningful and stable model.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C24(H24a,H24b), C25(H25a,H25b), C21(H21a,H21b), C20(H20a,H20b)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C5(H5), C3(H3)
2.c Idealised Me refined as rotating group:
 C23(H23a,H23b,H23c), C22(H22a,H22b,H22c), C26(H26a,H26b,H26c), C19(H19a,H19b,
 H19c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
F17 F 0.03945(14) 0.84670(10) 0.07745(9) 0.0272(3) Uani 1.000000 .
F10 F 0.19483(14) 0.85402(9) 0.42551(8) 0.0246(3) Uani 1.000000 .
F18 F 0.28538(13) 0.75607(9) 0.08667(8) 0.0241(3) Uani 1.000000 .
F1 F 0.04373(13) 0.68650(9) 0.22968(8) 0.0257(3) Uani 1.000000 .
F11 F 0.38976(14) 0.92158(11) 0.37892(9) 0.0302(3) Uani 1.000000 .
F8 F 0.43865(15) 0.63753(11) 0.45794(8) 0.0303(3) Uani 1.000000 .
F12 F 0.15614(16) 1.02446(10) 0.45471(8) 0.0307(3) Uani 1.000000 .
F9 F 0.53810(15) 0.69055(10) 0.31931(8) 0.0274(3) Uani 1.000000 .
F2 F 0.13252(16) 0.55426(12) 0.13106(9) 0.0378(3) Uani 1.000000 .
F16 F 0.23588(17) 0.89237(11) -0.01273(8) 0.0347(3) Uani 1.000000 .
F7 F 0.67687(14) 0.54192(11) 0.38238(10) 0.0357(3) Uani 1.000000 .
O2 O -0.08203(15) 0.77429(11) 0.42060(9) 0.0199(3) Uani 1.000000 .
O1 O 0.61822(16) 0.70266(12) 0.11597(10) 0.0234(3) Uani 1.000000 .
F3 F -0.01590(15) 0.53730(12) 0.26698(11) 0.0413(4) Uani 1.000000 .
F15 F -0.06596(18) 1.27629(11) 0.10482(11) 0.0413(3) Uani 1.000000 .
F14 F 0.14809(19) 1.29050(11) 0.12933(11) 0.0429(4) Uani 1.000000 .
F13 F -0.0630(2) 1.31460(11) 0.24317(10) 0.0490(4) Uani 1.000000 .
F4 F 0.6672(2) 0.19529(12) 0.23326(16) 0.0735(6) Uani 1.000000 .
F6 F 0.5554(3) 0.18971(14) 0.37850(15) 0.0826(7) Uani 1.000000 .
C14 C 0.1053(2) 1.05213(16) 0.12620(14) 0.0204(4) Uani 1.000000 .
C1 C 0.3171(2) 0.59403(15) 0.29449(12) 0.0164(4) Uani 1.000000 .
C3 C 0.3168(2) 0.40783(16) 0.26016(14) 0.0222(4) Uani 1.000000 .
C16 C 0.2297(2) 0.94678(16) 0.38803(13) 0.0204(4) Uani 1.000000 .
C9 C 0.5271(2) 0.59881(16) 0.37250(13) 0.0210(4) Uani 1.000000 .
C15 C 0.1654(2) 0.93947(15) 0.14892(13) 0.0180(4) Uani 1.000000 .
C2 C 0.2535(2) 0.52407(15) 0.26078(13) 0.0175(4) Uani 1.000000 .
F5 F 0.4336(2) 0.17905(12) 0.28075(19) 0.0755(7) Uani 1.000000 .
C12 C 0.1223(2) 1.09532(16) 0.27743(14) 0.0204(4) Uani 1.000000 .
C18 C 0.1818(2) 0.85986(16) 0.07552(13) 0.0209(4) Uani 1.000000 .
C4 C 0.4534(2) 0.35494(16) 0.29463(15) 0.0244(4) Uani 1.000000 .
C5 C 0.5231(2) 0.41762(16) 0.33067(14) 0.0222(4) Uani 1.000000 .
C10 C 0.2071(2) 0.89657(15) 0.23434(13) 0.0171(4) Uani 1.000000 .
C13 C 0.0831(2) 1.13007(15) 0.19146(14) 0.0213(4) Uani 1.000000 .
C7 C 0.1053(2) 0.57490(15) 0.22239(13) 0.0193(4) Uani 1.000000 .
C6 C 0.4541(2) 0.53292(15) 0.32979(13) 0.0184(4) Uani 1.000000 .
C11 C 0.1819(2) 0.98159(15) 0.29632(13) 0.0178(4) Uani 1.000000 .
C23 C -0.2136(2) 0.92403(16) 0.32439(15) 0.0258(4) Uani 1.000000 .
C17 C 0.0241(3) 1.25225(17) 0.16764(16) 0.0293(5) Uani 1.000000 .
C24 C -0.2341(2) 0.83567(17) 0.39723(15) 0.0243(4) Uani 1.000000 .
C8 C 0.5289(3) 0.23086(18) 0.29364(18) 0.0334(5) Uani 1.000000 .
C25 C -0.1060(3) 0.70000(19) 0.49878(15) 0.0295(5) Uani 1.000000 .
C22 C 0.6225(3) 0.52846(19) 0.06712(16) 0.0308(5) Uani 1.000000 .
C21 C 0.7182(2) 0.58776(19) 0.09685(16) 0.0298(5) Uani 1.000000 .
C26 C 0.0498(3) 0.6411(2) 0.52743(16) 0.0347(5) Uani 1.000000 .
C19 C 0.6145(3) 0.8912(2) 0.11728(19) 0.0388(5) Uani 1.000000 .
C20 C 0.7138(3) 0.77085(19) 0.12134(16) 0.0306(5) Uani 1.000000 .
Li1 Li 0.3991(4) 0.7318(3) 0.2041(2) 0.0220(6) Uani 1.000000 .
Li2 Li 0.1311(4) 0.7608(3) 0.3316(2) 0.0216(6) Uani 1.000000 .
H12 H 0.1086(2) 1.14817(16) 0.32249(14) 0.0245(5) Uiso 1.000000 R
H14 H 0.0798(2) 1.07515(16) 0.06690(14) 0.0245(5) Uiso 1.000000 R
H5 H 0.6160(2) 0.38231(16) 0.35534(14) 0.0267(5) Uiso 1.000000 R
H3 H 0.2670(2) 0.36570(16) 0.23648(14) 0.0266(5) Uiso 1.000000 R
H23a H -0.1355(14) 0.88907(18) 0.2670(4) 0.0387(6) Uiso 1.000000 GR
H23b H -0.3184(4) 0.9659(9) 0.3099(8) 0.0387(6) Uiso 1.000000 GR
H23c H -0.1736(18) 0.9749(8) 0.3487(4) 0.0387(6) Uiso 1.000000 GR
H24a H -0.2743(2) 0.78408(17) 0.37274(15) 0.0292(5) Uiso 1.000000 R
H24b H -0.3154(2) 0.87067(17) 0.45464(15) 0.0292(5) Uiso 1.000000 R
H25a H -0.1882(3) 0.74275(19) 0.55265(15) 0.0355(5) Uiso 1.000000 R
H25b H -0.1471(3) 0.64454(19) 0.48103(15) 0.0355(5) Uiso 1.000000 R
H22a H 0.5846(17) 0.5666(8) 0.0119(7) 0.0462(7) Uiso 1.000000 GR
H22b H 0.6912(7) 0.4514(4) 0.0511(12) 0.0462(7) Uiso 1.000000 GR
H22c H 0.5289(12) 0.5285(12) 0.1189(4) 0.0462(7) Uiso 1.000000 GR
H21a H 0.8164(2) 0.58433(19) 0.04618(16) 0.0358(5) Uiso 1.000000 R
H21b H 0.7532(2) 0.55138(19) 0.15415(16) 0.0358(5) Uiso 1.000000 R
H26a H 0.1291(8) 0.5954(12) 0.4753(5) 0.0521(8) Uiso 1.000000 GR
H26b H 0.0920(11) 0.6961(2) 0.5432(12) 0.0521(8) Uiso 1.000000 GR
H26c H 0.0303(5) 0.5932(12) 0.5826(8) 0.0521(8) Uiso 1.000000 GR
H19a H 0.5751(19) 0.9064(4) 0.0595(7) 0.0581(8) Uiso 1.000000 GR
H19b H 0.5218(13) 0.9088(4) 0.1722(7) 0.0581(8) Uiso 1.000000 GR
H19c H 0.6814(7) 0.9372(2) 0.1175(14) 0.0581(8) Uiso 1.000000 GR
H20a H 0.7498(3) 0.75431(19) 0.18095(16) 0.0367(6) Uiso 1.000000 R
H20b H 0.8114(3) 0.75378(19) 0.06820(16) 0.0367(6) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F17 C18 1.349(2) .
F10 C16 1.357(2) .
F10 Li2 2.211(3) .
F18 C18 1.356(2) .
F18 Li1 2.174(3) .
F1 C7 1.345(2) .
F1 Li2 2.281(3) .
F11 C16 1.343(2) .
F8 C9 1.339(2) .
F12 C16 1.339(2) .
F9 C9 1.358(2) .
F9 Li1 2.277(3) .
F2 C7 1.337(2) .
F16 C18 1.338(2) .
F7 C9 1.336(2) .
O2 C24 1.439(2) .
O2 C25 1.433(2) .
O2 Li2 1.990(3) .
O1 C21 1.445(3) .
O1 C20 1.444(2) .
O1 Li1 2.000(3) .
F3 C7 1.337(2) .
F15 C17 1.330(3) .
F14 C17 1.344(3) .
F13 C17 1.335(3) .
F4 C8 1.293(3) .
F6 C8 1.349(3) .
C14 C15 1.391(3) .
C14 C13 1.383(3) .
C1 C2 1.405(3) .
C1 C6 1.413(2) .
C1 Li1 2.306(4) .
C1 Li2 2.226(4) .
C3 C2 1.395(3) .
C3 C4 1.384(3) .
C16 C11 1.498(3) .
C9 C6 1.500(3) .
C15 C18 1.504(3) .
C15 C10 1.406(3) .
C2 C7 1.501(2) .
F5 C8 1.313(3) .
C12 C13 1.387(3) .
C12 C11 1.390(3) .
C4 C5 1.391(3) .
C4 C8 1.494(3) .
C5 C6 1.388(3) .
C10 C11 1.410(3) .
C10 Li1 2.216(4) .
C10 Li2 2.307(4) .
C13 C17 1.501(3) .
C23 C24 1.498(3) .
C25 C26 1.497(3) .
C22 C21 1.496(3) .
C19 C20 1.493(3) .
Li1 Li2 2.585(4) .

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
Li2 F10 C16 116.43(13) . .
Li1 F18 C18 116.30(13) . .
Li2 F1 C7 115.52(13) . .
Li1 F9 C9 114.54(13) . .
C25 O2 C24 110.19(14) . .
Li2 O2 C24 122.51(14) . .
Li2 O2 C25 124.57(14) . .
C20 O1 C21 111.62(15) . .
Li1 O1 C21 117.60(15) . .
Li1 O1 C20 119.07(15) . .
C13 C14 C15 118.82(17) . .
C6 C1 C2 112.05(16) . .
Li1 C1 C2 123.53(15) . .
Li1 C1 C6 102.67(14) . .
Li2 C1 C2 111.33(14) . .
Li2 C1 C6 131.40(16) . .
Li2 C1 Li1 69.51(12) . .
C4 C3 C2 118.87(18) . .
F11 C16 F10 105.65(15) . .
F12 C16 F10 106.07(15) . .
F12 C16 F11 106.05(15) . .
C11 C16 F10 112.04(15) . .
C11 C16 F11 112.56(15) . .
C11 C16 F12 113.85(16) . .
F9 C9 F8 105.28(15) . .
F7 C9 F8 106.35(15) . .
F7 C9 F9 106.04(15) . .
C6 C9 F8 112.94(15) . .
C6 C9 F9 111.62(15) . .
C6 C9 F7 113.97(16) . .
C18 C15 C14 115.72(16) . .
C10 C15 C14 125.16(17) . .
C10 C15 C18 119.10(16) . .
C3 C2 C1 125.12(17) . .
C7 C2 C1 119.30(16) . .
C7 C2 C3 115.58(16) . .
C11 C12 C13 118.66(17) . .
F18 C18 F17 105.75(15) . .
F16 C18 F17 105.69(15) . .
F16 C18 F18 106.15(15) . .
C15 C18 F17 112.42(16) . .
C15 C18 F18 112.78(15) . .
C15 C18 F16 113.42(15) . .
C5 C4 C3 119.91(18) . .
C8 C4 C3 121.27(19) . .
C8 C4 C5 118.82(18) . .
C6 C5 C4 118.51(17) . .
C11 C10 C15 112.24(16) . .
Li1 C10 C15 107.23(15) . .
Li1 C10 C11 131.73(15) . .
Li2 C10 C15 127.99(15) . .
Li2 C10 C11 104.27(15) . .
Li2 C10 Li1 69.66(12) . .
C12 C13 C14 120.00(17) . .
C17 C13 C14 120.06(18) . .
C17 C13 C12 119.88(18) . .
F2 C7 F1 105.68(15) . .
F3 C7 F1 105.75(15) . .
F3 C7 F2 105.87(16) . .
C2 C7 F1 113.16(15) . .
C2 C7 F2 113.17(15) . .
C2 C7 F3 112.55(15) . .
C9 C6 C1 116.78(16) . .
C5 C6 C1 125.52(17) . .
C5 C6 C9 117.68(16) . .
C12 C11 C16 117.35(16) . .
C10 C11 C16 117.48(16) . .
C10 C11 C12 125.12(17) . .
F14 C17 F15 105.52(18) . .
F13 C17 F15 107.44(18) . .
F13 C17 F14 105.95(17) . .
C13 C17 F15 113.04(17) . .
C13 C17 F14 111.67(17) . .
C13 C17 F13 112.70(18) . .
C23 C24 O2 110.35(15) . .
F6 C8 F4 106.4(2) . .
F5 C8 F4 109.0(2) . .
F5 C8 F6 101.7(2) . .
C4 C8 F4 113.78(19) . .
C4 C8 F6 111.5(2) . .
C4 C8 F5 113.52(18) . .
C26 C25 O2 110.52(16) . .
C22 C21 O1 109.03(16) . .
C19 C20 O1 109.63(17) . .
F9 Li1 F18 174.07(17) . .
O1 Li1 F18 91.24(14) . .
O1 Li1 F9 84.58(12) . .
C1 Li1 F18 103.72(14) . .
C1 Li1 F9 75.28(11) . .
C1 Li1 O1 123.21(16) . .
C10 Li1 F18 77.58(12) . .
C10 Li1 F9 108.30(15) . .
C10 Li1 O1 126.24(17) . .
C10 Li1 C1 110.51(14) . .
Li2 Li1 F18 94.41(14) . .
Li2 Li1 F9 89.67(13) . .
Li2 Li1 O1 174.14(18) . .
Li2 Li1 C1 53.79(11) . .
Li2 Li1 C10 56.83(11) . .
F1 Li2 F10 172.58(16) . .
O2 Li2 F10 92.27(14) . .
O2 Li2 F1 85.98(12) . .
C1 Li2 F10 112.77(14) . .
C1 Li2 F1 74.18(11) . .
C1 Li2 O2 120.58(16) . .
C10 Li2 F10 76.07(11) . .
C10 Li2 F1 99.38(13) . .
C10 Li2 O2 128.37(16) . .
C10 Li2 C1 110.11(14) . .
Li1 Li2 F10 93.98(13) . .
Li1 Li2 F1 87.81(13) . .
Li1 Li2 O2 173.75(18) . .
Li1 Li2 C1 56.71(11) . .
Li1 Li2 C10 53.51(11) . .

_database_code_depnum_ccdc_archive 'CCDC 1010408'
#######################################################################
#
#                 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_13S063
_audit_creation_date             2013-05-23
_audit_creation_method           
;
  Olex2 1.2-beta
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_chemical_formula_moiety         'C28 H17 B F18'
_chemical_formula_sum            'C28 H17 B F18'
_chemical_formula_weight         706.24
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_cell_length_a                   9.1239(3)
_cell_length_b                   24.4308(8)
_cell_length_c                   12.5042(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.114(1)
_cell_angle_gamma                90
_cell_volume                     2765.78(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9907
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      2.34
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_correction_T_min  0.9522
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0900 before and 0.0487 after correction.
The Ratio of minimum to maximum transmission is 0.9714.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.6959
_exptl_crystal_density_meas      .
_exptl_crystal_description       prism
_exptl_crystal_F_000             1409.5370
_exptl_crystal_preparation       'soaked in perfluoro polyether oil'
_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.241
_exptl_crystal_size_min          0.184
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            46204
_diffrn_reflns_theta_full        25.9995
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.34
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.9996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTON area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -11
_reflns_limit_k_max              30
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              -7
_reflns_number_gt                4871
_reflns_number_total             5438
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         1.1343
_refine_diff_density_min         -1.0343
_refine_diff_density_rms         0.1223
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             8.7049
_refine_ls_goodness_of_fit_ref   1.0564
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     426
_refine_ls_number_reflns         5438
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0543
_refine_ls_restrained_S_all      1.0564
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0887P)²+3.0254P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1489
_refine_special_details          
'The CF3 group around C27 shows rotational disorder which could not be modelled as a physically stable disordered model. This causes the high residual peaks in the Fourier maps.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C22(H22), C2(H2), C6(H6), C15(H15), C5(H5), C13(H13), C24(H24)
2.b Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c), C8(H8a,H8b,H8c), C10(H10a,H10b,H10c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
F18 F 0.14451(14) 0.33237(5) 0.80030(9) 0.0235(3) Uani 1.000000 .
F7 F 0.11076(15) 0.24041(5) 0.88360(11) 0.0272(3) Uani 1.000000 .
F1 F 0.62497(14) 0.33443(5) 1.08337(11) 0.0270(3) Uani 1.000000 .
F15 F -0.20812(15) 0.39520(6) 1.25264(11) 0.0289(3) Uani 1.000000 .
F16 F -0.08156(14) 0.35153(6) 0.81210(11) 0.0308(3) Uani 1.000000 .
F14 F -0.25683(15) 0.44049(6) 1.10496(12) 0.0313(3) Uani 1.000000 .
F17 F 0.07938(17) 0.41591(5) 0.81909(11) 0.0302(3) Uani 1.000000 .
F8 F 0.09864(15) 0.15507(5) 0.92218(13) 0.0332(3) Uani 1.000000 .
F9 F 0.08482(14) 0.21576(6) 1.04475(11) 0.0307(3) Uani 1.000000 .
F10 F 0.43242(15) 0.31693(7) 1.20962(11) 0.0336(3) Uani 1.000000 .
F12 F 0.28431(17) 0.31787(7) 1.33041(11) 0.0377(4) Uani 1.000000 .
F3 F 0.76113(16) 0.27044(6) 1.15602(13) 0.0385(4) Uani 1.000000 .
F11 F 0.28383(18) 0.25007(6) 1.22173(12) 0.0377(4) Uani 1.000000 .
F13 F -0.08623(16) 0.46814(6) 1.22657(15) 0.0439(4) Uani 1.000000 .
F2 F 0.76166(16) 0.28866(6) 0.98798(14) 0.0389(4) Uani 1.000000 .
F6 F 0.5265(3) 0.05144(7) 1.07593(18) 0.0628(6) Uani 1.000000 .
C22 C 0.5412(2) 0.42974(8) 0.79008(16) 0.0155(4) Uani 1.000000 .
F4 F 0.6133(4) 0.06834(8) 0.93232(15) 0.0943(11) Uani 1.000000 .
C21 C 0.4677(2) 0.44604(8) 0.87662(16) 0.0171(4) Uani 1.000000 .
H21 H 0.4630(2) 0.48384(8) 0.89366(16) 0.0205(5) Uiso 1.000000 R
C13 C -0.0346(2) 0.38992(8) 1.12793(17) 0.0174(4) Uani 1.000000 .
C2 C 0.5566(2) 0.24100(8) 1.03708(16) 0.0160(4) Uani 1.000000 .
C19 C 0.4105(2) 0.35169(8) 0.91886(16) 0.0157(4) Uani 1.000000 .
C5 C 0.3816(2) 0.14946(8) 0.99337(16) 0.0178(4) Uani 1.000000 .
H5 H 0.3208(2) 0.11817(8) 0.97812(16) 0.0214(5) Uiso 1.000000 R
C20 C 0.4020(2) 0.40839(8) 0.93765(16) 0.0169(4) Uani 1.000000 .
H20 H 0.3496(2) 0.42103(8) 0.99392(16) 0.0203(5) Uiso 1.000000 R
C10 C 0.1929(2) 0.33301(8) 1.03765(15) 0.0137(4) Uani 1.000000 .
C6 C 0.3196(2) 0.20139(8) 0.98696(15) 0.0152(4) Uani 1.000000 .
C11 C 0.1817(2) 0.33338(8) 1.14970(16) 0.0161(4) Uani 1.000000 .
C24 C 0.4890(2) 0.33546(8) 0.83434(17) 0.0180(4) Uani 1.000000 .
H24 H 0.5005(2) 0.29756(8) 0.82067(17) 0.0216(5) Uiso 1.000000 R
C14 C -0.0333(2) 0.38882(8) 1.01818(17) 0.0180(4) Uani 1.000000 .
H14 H -0.1085(2) 0.40722(8) 0.97246(17) 0.0216(5) Uiso 1.000000 R
C15 C 0.0780(2) 0.36078(8) 0.97342(16) 0.0150(4) Uani 1.000000 .
C18 C 0.0578(2) 0.36439(9) 0.85133(17) 0.0192(4) Uani 1.000000 .
C23 C 0.5500(2) 0.37352(8) 0.77042(16) 0.0180(4) Uani 1.000000 .
H23 H 0.5987(2) 0.36116(8) 0.71202(16) 0.0217(5) Uiso 1.000000 R
C25 C 0.6084(2) 0.47328(8) 0.72273(16) 0.0178(4) Uani 1.000000 .
F5 F 0.7329(2) 0.08661(8) 1.0833(3) 0.1002(11) Uani 1.000000 .
C12 C 0.0710(2) 0.36110(8) 1.19420(16) 0.0177(4) Uani 1.000000 .
H12 H 0.0678(2) 0.36027(8) 1.26983(16) 0.0212(5) Uiso 1.000000 R
C1 C 0.4040(2) 0.24995(8) 1.00614(15) 0.0136(4) Uani 1.000000 .
C3 C 0.6190(2) 0.18892(8) 1.04514(16) 0.0178(4) Uani 1.000000 .
H3 H 0.7220(2) 0.18482(8) 1.06670(16) 0.0214(5) Uiso 1.000000 R
C4 C 0.5319(2) 0.14330(8) 1.02195(16) 0.0186(4) Uani 1.000000 .
C7 C 0.6731(2) 0.28454(9) 1.06601(19) 0.0227(5) Uani 1.000000 .
C16 C 0.2946(2) 0.30451(10) 1.22791(17) 0.0237(5) Uani 1.000000 .
C17 C -0.1469(2) 0.42340(9) 1.17780(19) 0.0230(5) Uani 1.000000 .
C9 C 0.1535(2) 0.20326(8) 0.95907(17) 0.0201(4) Uani 1.000000 .
C8 C 0.6011(3) 0.08737(9) 1.02672(19) 0.0250(5) Uani 1.000000 .
B1 B 0.3355(2) 0.31027(9) 0.98810(17) 0.0145(4) Uani 1.000000 .
C27 C 0.7365(3) 0.50121(10) 0.79285(19) 0.0280(5) Uani 1.000000 .
H27a H 0.7003(5) 0.5173(7) 0.8565(8) 0.0420(8) Uiso 1.000000 GR
H27b H 0.8133(9) 0.47414(18) 0.8157(12) 0.0420(8) Uiso 1.000000 GR
H27c H 0.7778(14) 0.5301(5) 0.7512(5) 0.0420(8) Uiso 1.000000 GR
C26 C 0.4925(3) 0.51640(11) 0.6834(2) 0.0344(6) Uani 1.000000 .
H26a H 0.4078(10) 0.49857(15) 0.6417(14) 0.0516(9) Uiso 1.000000 GR
H26c H 0.4598(17) 0.5352(6) 0.7456(2) 0.0516(9) Uiso 1.000000 GR
H26b H 0.5357(7) 0.5431(5) 0.6379(14) 0.0516(9) Uiso 1.000000 GR
C28 C 0.6693(3) 0.44820(10) 0.6251(2) 0.0339(6) Uani 1.000000 .
H28a H 0.7480(16) 0.4222(6) 0.6497(2) 0.0508(9) Uiso 1.000000 GR
H28b H 0.5898(6) 0.4291(7) 0.5800(9) 0.0508(9) Uiso 1.000000 GR
H28c H 0.709(2) 0.47728(14) 0.5830(9) 0.0508(9) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F18 C18 1.330(3) .
F7 C9 1.332(2) .
F1 C7 1.323(3) .
F15 C17 1.339(3) .
F16 C18 1.342(2) .
F14 C17 1.336(3) .
F17 C18 1.344(2) .
F8 C9 1.339(2) .
F9 C9 1.342(3) .
F10 C16 1.340(3) .
F12 C16 1.337(2) .
F3 C7 1.344(3) .
F11 C16 1.335(3) .
F13 C17 1.338(3) .
F2 C7 1.345(3) .
F6 C8 1.310(3) .
C22 C21 1.400(3) .
C22 C23 1.399(3) .
C22 C25 1.531(3) .
F4 C8 1.286(3) .
C21 C20 1.379(3) .
C13 C14 1.374(3) .
C13 C12 1.383(3) .
C13 C17 1.506(3) .
C2 C1 1.414(3) .
C2 C3 1.393(3) .
C2 C7 1.516(3) .
C19 C20 1.409(3) .
C19 C24 1.405(3) .
C19 B1 1.546(3) .
C5 C6 1.387(3) .
C5 C4 1.382(3) .
C10 C11 1.417(3) .
C10 C15 1.413(3) .
C10 B1 1.607(3) .
C6 C1 1.419(3) .
C6 C9 1.513(3) .
C11 C12 1.388(3) .
C11 C16 1.505(3) .
C24 C23 1.387(3) .
C14 C15 1.398(3) .
C15 C18 1.517(3) .
C25 C27 1.532(3) .
C25 C26 1.530(3) .
C25 C28 1.531(3) .
F5 C8 1.318(3) .
C1 B1 1.606(3) .
C3 C4 1.379(3) .
C4 C8 1.503(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
C23 C22 C21 117.27(18) . .
C25 C22 C21 119.37(17) . .
C25 C22 C23 123.36(18) . .
C20 C21 C22 121.40(18) . .
C12 C13 C14 119.81(18) . .
C17 C13 C14 120.97(19) . .
C17 C13 C12 119.20(19) . .
C3 C2 C1 122.75(18) . .
C7 C2 C1 126.45(18) . .
C7 C2 C3 110.79(18) . .
C24 C19 C20 116.52(18) . .
B1 C19 C20 120.86(18) . .
B1 C19 C24 122.62(18) . .
C4 C5 C6 119.94(19) . .
C19 C20 C21 121.80(18) . .
C15 C10 C11 114.81(17) . .
B1 C10 C11 122.96(17) . .
B1 C10 C15 121.73(17) . .
C1 C6 C5 123.08(18) . .
C9 C6 C5 115.51(17) . .
C9 C6 C1 121.42(17) . .
C12 C11 C10 122.98(18) . .
C16 C11 C10 120.79(17) . .
C16 C11 C12 116.20(18) . .
C23 C24 C19 121.50(18) . .
C15 C14 C13 120.37(18) . .
C14 C15 C10 122.17(18) . .
C18 C15 C10 126.07(18) . .
C18 C15 C14 111.76(17) . .
F16 C18 F18 106.25(17) . .
F17 C18 F18 106.80(17) . .
F17 C18 F16 106.08(16) . .
C15 C18 F18 116.30(16) . .
C15 C18 F16 110.21(17) . .
C15 C18 F17 110.62(17) . .
C24 C23 C22 121.42(18) . .
C27 C25 C22 108.88(17) . .
C26 C25 C22 110.31(17) . .
C26 C25 C27 108.96(19) . .
C28 C25 C22 111.74(17) . .
C28 C25 C27 107.96(19) . .
C28 C25 C26 108.9(2) . .
C11 C12 C13 119.70(19) . .
C6 C1 C2 114.35(17) . .
B1 C1 C2 122.23(17) . .
B1 C1 C6 123.33(17) . .
C4 C3 C2 120.22(19) . .
C3 C4 C5 119.61(19) . .
C8 C4 C5 120.51(19) . .
C8 C4 C3 119.88(19) . .
F3 C7 F1 105.97(18) . .
F2 C7 F1 106.96(18) . .
F2 C7 F3 106.06(18) . .
C2 C7 F1 116.62(17) . .
C2 C7 F3 110.40(18) . .
C2 C7 F2 110.24(18) . .
F12 C16 F10 106.70(18) . .
F11 C16 F10 106.25(18) . .
F11 C16 F12 106.57(19) . .
C11 C16 F10 111.34(18) . .
C11 C16 F12 112.61(18) . .
C11 C16 F11 112.92(18) . .
F14 C17 F15 107.13(17) . .
F13 C17 F15 106.67(19) . .
F13 C17 F14 106.80(18) . .
C13 C17 F15 111.98(18) . .
C13 C17 F14 112.31(18) . .
C13 C17 F13 111.61(17) . .
F8 C9 F7 106.92(17) . .
F9 C9 F7 106.61(17) . .
F9 C9 F8 106.49(17) . .
C6 C9 F7 112.38(17) . .
C6 C9 F8 111.95(17) . .
C6 C9 F9 112.10(17) . .
F4 C8 F6 107.3(2) . .
F5 C8 F6 103.4(2) . .
F5 C8 F4 108.1(3) . .
C4 C8 F6 112.81(19) . .
C4 C8 F4 112.06(19) . .
C4 C8 F5 112.6(2) . .
C10 B1 C19 115.18(17) . .
C1 B1 C19 119.17(17) . .
C1 B1 C10 125.65(17) . .

_database_code_depnum_ccdc_archive 'CCDC 1010409'
#######################################################################
#
#                 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_13S090
_audit_creation_date             2013-07-24
_audit_creation_method           
;
  Olex2 1.2-beta
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_chemical_formula_moiety         'C36 H36 B N'
_chemical_formula_sum            'C36 H36 B N'
_chemical_formula_weight         493.52
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_cell_length_a                   8.8391(3)
_cell_length_b                   34.0268(11)
_cell_length_c                   9.5807(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.720(1)
_cell_angle_gamma                90
_cell_volume                     2831.26(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.11
_cell_measurement_theta_min      2.39
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9381
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0868 before and 0.0509 after correction.
The Ratio of minimum to maximum transmission is 0.9381.
The λ/2 correction factor is 0.0000.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.1577
_exptl_crystal_density_meas      .
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056.3818
_exptl_crystal_preparation       'soaked in perfluoro polyether oil'
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.133
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            31666
_diffrn_reflns_theta_full        25.9925
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.24
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTON area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -10
_reflns_limit_k_max              41
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              -6
_reflns_number_gt                4703
_reflns_number_total             5556
_reflns_threshold_expression     I>=2u(I)
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.2459
_refine_diff_density_min         -0.3475
_refine_diff_density_rms         0.0847
_refine_ls_d_res_high            0.8109
_refine_ls_d_res_low             9.0727
_refine_ls_goodness_of_fit_ref   1.0575
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    60
_refine_ls_number_parameters     348
_refine_ls_number_reflns         5556
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.0575
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0683P)²+1.1350P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1265
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C35(H35), C23(H23), C21(H21), C20(H20), C32(H32), C28(H28), C34(H34),
 C36(H36), C24(H24), C26(H26), C30(H30), C12(H12), C27(H27), C29(H29), C3(H3),
 C33(H33), C5(H5), C14(H14)
2.b Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C16(H16a,H16b,H16c), C18(H18a,H18b,H18c), C9(H9a,H9b,H9c),
 C8(H8a,H8b,H8c), C17(H17a,H17b,H17c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
N1 N 0.61232(13) 0.28907(3) -0.15128(13) 0.0187(3) Uani 1.000000 .
C1 C 1.07893(16) 0.41980(4) 0.22344(16) 0.0189(3) Uani 1.000000 .
C2 C 1.21785(16) 0.41694(4) 0.32326(16) 0.0188(3) Uani 1.000000 .
C3 C 1.35713(16) 0.42821(4) 0.28634(16) 0.0206(3) Uani 1.000000 .
H3 H 1.44969(16) 0.42559(4) 0.35423(16) 0.0248(4) Uiso 1.000000 R
C4 C 1.36348(16) 0.44319(4) 0.15233(17) 0.0209(3) Uani 1.000000 .
C5 C 1.22586(17) 0.44731(4) 0.05605(16) 0.0225(3) Uani 1.000000 .
H5 H 1.22791(17) 0.45819(4) -0.03489(16) 0.0270(4) Uiso 1.000000 R
C6 C 1.08533(17) 0.43599(4) 0.08861(16) 0.0214(3) Uani 1.000000 .
C7 C 1.22092(17) 0.40058(5) 0.47045(16) 0.0242(3) Uani 1.000000 .
H7a H 1.1538(10) 0.4164(2) 0.5190(5) 0.0363(5) Uiso 1.000000 GR
H7b H 1.1844(12) 0.37333(11) 0.46315(16) 0.0363(5) Uiso 1.000000 GR
H7c H 1.3265(3) 0.4014(3) 0.5246(4) 0.0363(5) Uiso 1.000000 GR
C8 C 1.51359(17) 0.45552(5) 0.11333(18) 0.0268(3) Uani 1.000000 .
H8a H 1.5271(7) 0.48394(7) 0.1270(12) 0.0402(5) Uiso 1.000000 GR
H8b H 1.5986(2) 0.4417(3) 0.1739(8) 0.0402(5) Uiso 1.000000 GR
H8c H 1.5129(5) 0.4490(3) 0.0136(4) 0.0402(5) Uiso 1.000000 GR
C9 C 0.94302(18) 0.44284(5) -0.02384(17) 0.0282(4) Uani 1.000000 .
H9a H 0.9380(7) 0.4230(2) -0.0988(7) 0.0423(5) Uiso 1.000000 GR
H9b H 0.8511(2) 0.4408(3) 0.0193(3) 0.0423(5) Uiso 1.000000 GR
H9c H 0.9478(7) 0.46910(14) -0.0648(9) 0.0423(5) Uiso 1.000000 GR
C10 C 0.85020(16) 0.41601(4) 0.38812(16) 0.0195(3) Uani 1.000000 .
C11 C 0.82240(16) 0.45637(4) 0.41066(16) 0.0224(3) Uani 1.000000 .
C12 C 0.74206(17) 0.46759(5) 0.51632(17) 0.0262(3) Uani 1.000000 .
H12 H 0.72118(17) 0.49468(5) 0.52742(17) 0.0314(4) Uiso 1.000000 R
C13 C 0.69161(17) 0.44058(5) 0.60570(17) 0.0268(4) Uani 1.000000 .
C14 C 0.72597(17) 0.40122(5) 0.58890(16) 0.0258(3) Uani 1.000000 .
H14 H 0.69651(17) 0.38236(5) 0.65192(16) 0.0310(4) Uiso 1.000000 R
C15 C 0.80244(16) 0.38860(4) 0.48222(16) 0.0217(3) Uani 1.000000 .
C16 C 0.87546(19) 0.48826(4) 0.32101(19) 0.0284(4) Uani 1.000000 .
H16a H 0.98821(19) 0.4895(2) 0.3405(10) 0.0427(5) Uiso 1.000000 GR
H16b H 0.8390(12) 0.48238(19) 0.22023(19) 0.0427(5) Uiso 1.000000 GR
H16c H 0.8336(11) 0.51361(7) 0.3441(9) 0.0427(5) Uiso 1.000000 GR
C17 C 0.6020(2) 0.45352(6) 0.7168(2) 0.0376(4) Uani 1.000000 .
H17a H 0.6583(8) 0.4745(3) 0.7747(10) 0.0564(7) Uiso 1.000000 GR
H17b H 0.5009(6) 0.4634(4) 0.6703(2) 0.0564(7) Uiso 1.000000 GR
H17c H 0.5883(14) 0.43116(11) 0.7777(9) 0.0564(7) Uiso 1.000000 GR
C18 C 0.83504(18) 0.34507(5) 0.47531(18) 0.0270(3) Uani 1.000000 .
H18a H 0.7504(7) 0.33228(7) 0.4106(10) 0.0405(5) Uiso 1.000000 GR
H18b H 0.9314(7) 0.34113(5) 0.4405(12) 0.0405(5) Uiso 1.000000 GR
H18c H 0.8444(13) 0.33359(8) 0.5704(3) 0.0405(5) Uiso 1.000000 GR
C19 C 0.84055(16) 0.37087(4) 0.15270(16) 0.0192(3) Uani 1.000000 .
C20 C 0.68353(16) 0.36219(4) 0.14066(15) 0.0189(3) Uani 1.000000 .
H20 H 0.62746(16) 0.37470(4) 0.20367(15) 0.0227(4) Uiso 1.000000 R
C21 C 0.60696(16) 0.33623(4) 0.04106(15) 0.0183(3) Uani 1.000000 .
H21 H 0.49982(16) 0.33181(4) 0.03507(15) 0.0219(4) Uiso 1.000000 R
C22 C 0.68652(16) 0.31640(4) -0.05110(15) 0.0177(3) Uani 1.000000 .
C23 C 0.84402(16) 0.32388(4) -0.03972(16) 0.0214(3) Uani 1.000000 .
H23 H 0.90090(16) 0.31044(4) -0.09991(16) 0.0257(4) Uiso 1.000000 R
C24 C 0.91724(16) 0.35061(4) 0.05813(16) 0.0214(3) Uani 1.000000 .
H24 H 1.02371(16) 0.35556(4) 0.06197(16) 0.0257(4) Uiso 1.000000 R
C25 C 0.69474(15) 0.25516(4) -0.18501(15) 0.0165(3) Uani 1.000000 .
C26 C 0.78325(16) 0.23299(4) -0.07784(15) 0.0206(3) Uani 1.000000 .
H26 H 0.79652(16) 0.24143(4) 0.01818(15) 0.0247(4) Uiso 1.000000 R
C27 C 0.85206(17) 0.19850(4) -0.11172(16) 0.0221(3) Uani 1.000000 .
H27 H 0.91307(17) 0.18344(4) -0.03870(16) 0.0265(4) Uiso 1.000000 R
C28 C 0.83223(17) 0.18591(4) -0.25169(16) 0.0217(3) Uani 1.000000 .
H28 H 0.87633(17) 0.16180(4) -0.27420(16) 0.0261(4) Uiso 1.000000 R
C29 C 0.74759(17) 0.20872(4) -0.35866(16) 0.0209(3) Uani 1.000000 .
H29 H 0.73636(17) 0.20053(4) -0.45484(16) 0.0251(4) Uiso 1.000000 R
C30 C 0.67939(16) 0.24334(4) -0.32604(15) 0.0186(3) Uani 1.000000 .
H30 H 0.62233(16) 0.25896(4) -0.39968(15) 0.0223(4) Uiso 1.000000 R
C31 C 0.44839(16) 0.28743(4) -0.18737(14) 0.0169(3) Uani 1.000000 .
C32 C 0.36283(17) 0.32128(4) -0.22923(15) 0.0197(3) Uani 1.000000 .
H32 H 0.41390(17) 0.34569(4) -0.23376(15) 0.0237(4) Uiso 1.000000 R
C33 C 0.20355(17) 0.31944(5) -0.26426(15) 0.0220(3) Uani 1.000000 .
H33 H 0.14588(17) 0.34274(5) -0.29013(15) 0.0264(4) Uiso 1.000000 R
C34 C 0.12763(16) 0.28368(5) -0.26176(15) 0.0214(3) Uani 1.000000 .
H34 H 0.01867(16) 0.28237(5) -0.28791(15) 0.0257(4) Uiso 1.000000 R
C35 C 0.21241(16) 0.25004(4) -0.22080(15) 0.0207(3) Uani 1.000000 .
H35 H 0.16112(16) 0.22558(4) -0.21861(15) 0.0249(4) Uiso 1.000000 R
C36 C 0.37169(16) 0.25173(4) -0.18289(15) 0.0187(3) Uani 1.000000 .
H36 H 0.42864(16) 0.22852(4) -0.15382(15) 0.0225(4) Uiso 1.000000 R
B1 B 0.92416(18) 0.40245(5) 0.25768(18) 0.0191(3) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C22 1.4080(18) .
N1 C25 1.4331(18) .
N1 C31 1.4268(17) .
C1 C2 1.412(2) .
C1 C6 1.415(2) .
C1 B1 1.579(2) .
C2 C3 1.396(2) .
C2 C7 1.512(2) .
C4 C3 1.392(2) .
C4 C5 1.390(2) .
C4 C8 1.504(2) .
C6 C5 1.390(2) .
C6 C9 1.514(2) .
C10 C11 1.419(2) .
C10 C15 1.415(2) .
C10 B1 1.583(2) .
C12 C11 1.394(2) .
C13 C12 1.385(2) .
C13 C14 1.389(2) .
C13 C17 1.506(2) .
C15 C14 1.394(2) .
C15 C18 1.513(2) .
C16 C11 1.512(2) .
C19 C20 1.403(2) .
C19 C24 1.409(2) .
C19 B1 1.561(2) .
C21 C20 1.382(2) .
C22 C21 1.400(2) .
C22 C23 1.3994(19) .
C23 C24 1.378(2) .
C25 C26 1.392(2) .
C25 C30 1.392(2) .
C26 C27 1.388(2) .
C28 C27 1.388(2) .
C28 C29 1.388(2) .
C30 C29 1.385(2) .
C31 C32 1.395(2) .
C31 C36 1.396(2) .
C32 C33 1.387(2) .
C34 C33 1.392(2) .
C35 C34 1.384(2) .
C35 C36 1.388(2) .

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
C22 N1 C25 119.58(11) . .
C22 N1 C31 120.95(11) . .
C25 N1 C31 116.74(11) . .
C6 C1 C2 117.87(13) . .
B1 C1 C2 120.74(13) . .
B1 C1 C6 121.22(13) . .
C3 C2 C1 120.40(14) . .
C3 C2 C7 118.28(13) . .
C7 C2 C1 121.29(13) . .
C2 C3 C4 121.52(13) . .
C5 C4 C3 117.93(13) . .
C8 C4 C3 121.35(13) . .
C8 C4 C5 120.71(14) . .
C6 C5 C4 122.09(14) . .
C5 C6 C1 120.12(13) . .
C9 C6 C1 122.71(13) . .
C9 C6 C5 117.15(14) . .
C11 C10 C15 117.41(14) . .
B1 C10 C11 120.72(13) . .
B1 C10 C15 121.79(13) . .
C12 C11 C10 120.12(15) . .
C16 C11 C10 121.84(14) . .
C16 C11 C12 118.04(14) . .
C11 C12 C13 122.24(14) . .
C14 C13 C12 117.74(14) . .
C17 C13 C12 121.01(15) . .
C17 C13 C14 121.25(16) . .
C13 C14 C15 121.88(15) . .
C14 C15 C10 120.47(14) . .
C18 C15 C10 122.39(14) . .
C18 C15 C14 117.12(14) . .
C24 C19 C20 115.55(13) . .
B1 C19 C20 122.72(13) . .
B1 C19 C24 121.64(13) . .
C21 C20 C19 122.79(13) . .
C20 C21 C22 120.31(13) . .
C21 C22 N1 121.56(12) . .
C21 C22 C23 118.18(13) . .
C23 C22 N1 120.25(12) . .
C24 C23 C22 120.50(13) . .
C19 C24 C23 122.63(13) . .
C26 C25 N1 120.64(13) . .
C30 C25 N1 119.32(13) . .
C30 C25 C26 119.96(13) . .
C27 C26 C25 119.77(13) . .
C26 C27 C28 120.34(14) . .
C29 C28 C27 119.64(14) . .
C30 C29 C28 120.42(14) . .
C29 C30 C25 119.79(13) . .
C32 C31 N1 120.61(12) . .
C36 C31 N1 120.25(12) . .
C36 C31 C32 119.14(13) . .
C33 C32 C31 120.26(13) . .
C34 C33 C32 120.42(13) . .
C33 C34 C35 119.37(13) . .
C36 C35 C34 120.61(13) . .
C35 C36 C31 120.19(13) . .
C10 B1 C1 123.78(13) . .
C10 B1 C19 119.59(13) . .
C19 B1 C1 116.62(13) . .

_database_code_depnum_ccdc_archive 'CCDC 1010410'
#######################################################################
#
#                 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_13S091
_audit_creation_date             2013-08-05
_audit_creation_method           
;
  Olex2 1.2-beta
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_chemical_formula_moiety         'C36 H18 B F18 N'
_chemical_formula_sum            'C36 H18 B F18 N'
_chemical_formula_weight         817.35
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      tetragonal
_space_group_IT_number           80
_space_group_name_H-M_alt        'I 41'
_space_group_name_Hall           'I 4bw'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -y+1/2,x,z+3/4
3 y+1/2,-x,z+3/4
4 -x,-y,z
5 x+1/2,y+1/2,z+1/2
6 -y+1,x+1/2,z+5/4
7 y+1,-x+1/2,z+5/4
8 -x+1/2,-y+1/2,z+1/2

_cell_length_a                   23.5023(11)
_cell_length_b                   23.5023(11)
_cell_length_c                   25.1820(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     13909.5(11)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.02
_cell_measurement_theta_min      2.45
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9326
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0820 before and 0.0529 after correction.
The Ratio of minimum to maximum transmission is 0.9326.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.5611
_exptl_crystal_density_meas      .
_exptl_crystal_description       prism
_exptl_crystal_F_000             6534.5067
_exptl_crystal_preparation       'cut and soaked in perfluoro polyether oil'
_exptl_crystal_size_max          0.277
_exptl_crystal_size_mid          0.241
_exptl_crystal_size_min          0.12
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            46880
_diffrn_reflns_theta_full        25.9910
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.37
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTON area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9982
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTON area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.997
_reflns_limit_h_max              28
_reflns_limit_h_min              -28
_reflns_limit_k_max              28
_reflns_limit_k_min              -28
_reflns_limit_l_max              31
_reflns_limit_l_min              -31
_reflns_number_gt                10671
_reflns_number_total             13657
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         1.6233
_refine_diff_density_min         -0.4478
_refine_diff_density_rms         0.1217
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_d_res_high            0.8109
_refine_ls_d_res_low             8.5909
_refine_ls_goodness_of_fit_ref   1.0630
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    72
_refine_ls_number_parameters     1008
_refine_ls_number_reflns         13657
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0628
_refine_ls_restrained_S_all      1.0630
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1273P)²+8.9191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1952
_refine_special_details          
'Residual electron density can be interpreted by highly disordered hexane. The solvent would show an occupancy of less than 10% and results in an unstable refinement model. Thus it has been omitted in the final structure.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C34B(H34B), C21B(H21B), C24B(H24B), C36B(H36B), C12B(H12B), C20B(H20B),
 C14B(H14B), C23B(H23B), C3B(H3B), C29B(H29B), C35B(H35B), C33B(H33B), C5B(H5B),
  C30B(H30B), C32B(H32B), C28B(H28B), C26B(H26B), C27B(H27B), C5A(H5A),
 C12A(H12A), C35A(H35A), C36A(H36A), C26A(H26A), C20A(H20A), C32A(H32A),
 C28A(H28A), C33A(H33A), C14A(H14A), C27A(H27A), C23A(H23A), C24A(H24A),
 C34A(H34A), C30A(H30A), C3A(H3A), C21A(H21A), C29A(H29A)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
_atom_site_disorder_group
F18B F 0.14587(11) 0.28705(11) 0.59418(10) 0.0247(6) Uani 1.000000 . .
F9B F 0.11178(13) 0.24171(12) 0.68589(12) 0.0340(7) Uani 1.000000 . .
F17B F 0.17149(14) 0.32481(11) 0.52037(12) 0.0371(7) Uani 1.000000 . .
F7B F 0.04924(13) 0.17689(15) 0.70126(14) 0.0440(8) Uani 1.000000 . .
F8B F 0.07681(11) 0.19250(12) 0.62165(12) 0.0306(7) Uani 1.000000 . .
F15B F 0.10519(13) 0.22493(14) 0.35127(11) 0.0385(7) Uani 1.000000 . .
F13B F 0.08423(14) 0.13585(13) 0.35567(12) 0.0391(7) Uani 1.000000 . .
C17B C 0.08145(19) 0.1853(2) 0.3817(2) 0.0286(11) Uani 1.000000 . .
N1B N 0.38279(17) 0.34115(17) 0.59298(16) 0.0251(9) Uani 1.000000 . .
F16B F 0.08313(13) 0.31087(13) 0.53747(14) 0.0421(8) Uani 1.000000 . .
F11B F 0.12964(17) 0.06607(12) 0.58015(13) 0.0493(9) Uani 1.000000 . .
C4B C 0.1827(2) 0.0770(2) 0.7372(2) 0.0339(13) Uani 1.000000 . .
C31B C 0.41107(18) 0.35604(19) 0.64156(18) 0.0194(9) Uani 1.000000 . .
F5B F 0.1656(4) 0.0698(2) 0.82808(19) 0.153(4) Uani 1.000000 . 1
C34B C 0.4666(2) 0.3860(2) 0.7349(2) 0.0281(11) Uani 1.000000 . .
H34B H 0.4854(2) 0.3964(2) 0.7669(2) 0.0337(13) Uiso 1.000000 R .
F14B F 0.02648(12) 0.19936(18) 0.38512(13) 0.0506(10) Uani 1.000000 . .
C10B C 0.15700(17) 0.17950(18) 0.53927(18) 0.0183(9) Uani 1.000000 . .
C21B C 0.31689(17) 0.28056(19) 0.54416(18) 0.0208(9) Uani 1.000000 . .
H21B H 0.33383(17) 0.29143(19) 0.51144(18) 0.0250(11) Uiso 1.000000 R .
F3B F 0.30551(16) 0.04475(15) 0.62992(15) 0.0560(10) Uani 1.000000 . .
C24B C 0.26899(18) 0.2455(2) 0.63929(18) 0.0214(10) Uani 1.000000 . .
H24B H 0.25387(18) 0.2328(2) 0.67221(18) 0.0257(12) Uiso 1.000000 R .
C1B C 0.18845(18) 0.14349(19) 0.64392(18) 0.0193(9) Uani 1.000000 . .
C36B C 0.43760(19) 0.3143(2) 0.6720(2) 0.0242(10) Uani 1.000000 . .
H36B H 0.43730(19) 0.2757(2) 0.6608(2) 0.0291(12) Uiso 1.000000 R .
C12B C 0.12226(18) 0.13064(19) 0.45856(19) 0.0205(9) Uani 1.000000 . .
H12B H 0.11657(18) 0.09636(19) 0.43929(19) 0.0246(11) Uiso 1.000000 R .
C22B C 0.33792(17) 0.30234(19) 0.59226(17) 0.0180(9) Uani 1.000000 . .
C20B C 0.27124(19) 0.2431(2) 0.54466(18) 0.0243(10) Uani 1.000000 . .
H20B H 0.25693(19) 0.2295(2) 0.51173(18) 0.0291(12) Uiso 1.000000 R .
C14B C 0.11321(18) 0.23184(19) 0.46511(19) 0.0212(10) Uani 1.000000 . .
H14B H 0.10048(18) 0.26686(19) 0.45048(19) 0.0255(12) Uiso 1.000000 R .
C2B C 0.2320(2) 0.1058(2) 0.65821(19) 0.0247(10) Uani 1.000000 . .
C23B C 0.31268(18) 0.2834(2) 0.63983(18) 0.0213(10) Uani 1.000000 . .
H23B H 0.32645(18) 0.2973(2) 0.67284(18) 0.0255(12) Uiso 1.000000 R .
F6B F 0.1475(3) -0.0006(2) 0.7833(2) 0.121(3) Uani 1.000000 . 1
C3B C 0.2288(2) 0.0720(2) 0.7043(2) 0.0279(11) Uani 1.000000 . .
H3B H 0.2583(2) 0.0459(2) 0.7125(2) 0.0335(13) Uiso 1.000000 R .
C16B C 0.1541(2) 0.0703(2) 0.5327(2) 0.0305(12) Uani 1.000000 . .
B1B B 0.1955(2) 0.1816(2) 0.5914(2) 0.0177(10) Uani 1.000000 . .
C29B C 0.4761(3) 0.4032(3) 0.4898(2) 0.0419(14) Uani 1.000000 . .
H29B H 0.5155(3) 0.4046(3) 0.4815(2) 0.0503(17) Uiso 1.000000 R .
C15B C 0.13716(17) 0.23063(18) 0.51525(18) 0.0176(9) Uani 1.000000 . .
C35B C 0.46469(19) 0.3298(2) 0.7193(2) 0.0297(11) Uani 1.000000 . .
H35B H 0.48188(19) 0.3015(2) 0.7409(2) 0.0356(14) Uiso 1.000000 R .
C19B C 0.24521(18) 0.22429(19) 0.59196(19) 0.0213(10) Uani 1.000000 . .
C33B C 0.4409(2) 0.4276(2) 0.7035(2) 0.0297(11) Uani 1.000000 . .
H33B H 0.4428(2) 0.4665(2) 0.7137(2) 0.0357(14) Uiso 1.000000 R .
F1B F 0.28619(14) 0.11408(15) 0.57759(12) 0.0494(9) Uani 1.000000 . .
C18B C 0.13538(19) 0.28756(19) 0.54246(18) 0.0212(10) Uani 1.000000 . .
F4B F 0.2279(2) 0.0197(4) 0.8009(3) 0.152(3) Uani 1.000000 . 1
C6B C 0.14254(19) 0.14616(19) 0.67985(19) 0.0220(10) Uani 1.000000 . .
C11B C 0.14542(18) 0.12871(19) 0.50977(19) 0.0205(9) Uani 1.000000 . .
C5B C 0.1400(2) 0.1141(2) 0.7258(2) 0.0276(11) Uani 1.000000 . .
H5B H 0.1086(2) 0.1180(2) 0.7493(2) 0.0331(13) Uiso 1.000000 R .
C7B C 0.2872(2) 0.0981(3) 0.6284(2) 0.0392(14) Uani 1.000000 . .
F12B F 0.13155(16) 0.03064(12) 0.50341(13) 0.0467(8) Uani 1.000000 . .
C30B C 0.4577(2) 0.3721(2) 0.5337(2) 0.0296(11) Uani 1.000000 . .
H30B H 0.4844(2) 0.3518(2) 0.5547(2) 0.0355(13) Uiso 1.000000 R .
F10B F 0.20803(15) 0.05795(15) 0.54161(17) 0.0620(10) Uani 1.000000 . .
C25B C 0.4004(2) 0.37077(18) 0.54644(18) 0.0225(10) Uani 1.000000 . .
C32B C 0.41255(19) 0.4124(2) 0.6575(2) 0.0239(10) Uani 1.000000 . .
H32B H 0.39403(19) 0.4407(2) 0.6369(2) 0.0287(12) Uiso 1.000000 R .
C13B C 0.10775(18) 0.1818(2) 0.43609(18) 0.0214(10) Uani 1.000000 . .
F2B F 0.32869(13) 0.13054(17) 0.65102(15) 0.0549(9) Uani 1.000000 . .
C8B C 0.1803(3) 0.0424(2) 0.7867(3) 0.0432(14) Uani 1.000000 . .
C28B C 0.4380(3) 0.4315(2) 0.4585(2) 0.0405(14) Uani 1.000000 . .
H28B H 0.4509(3) 0.4527(2) 0.4286(2) 0.0486(17) Uiso 1.000000 R .
C26B C 0.3616(2) 0.4004(2) 0.5155(2) 0.0332(12) Uani 1.000000 . .
H26B H 0.3224(2) 0.4010(2) 0.5247(2) 0.0398(14) Uiso 1.000000 R .
C9B C 0.0950(2) 0.1891(2) 0.6716(2) 0.0265(11) Uani 1.000000 . .
C27B C 0.3808(3) 0.4293(2) 0.4706(2) 0.0414(15) Uani 1.000000 . .
H27B H 0.3542(3) 0.4477(2) 0.4480(2) 0.0497(17) Uiso 1.000000 R .
F18A F 0.34964(11) 0.71752(10) 0.46011(10) 0.0238(6) Uani 1.000000 . .
F8A F 0.42392(11) 0.80664(13) 0.43233(12) 0.0321(7) Uani 1.000000 . .
F17A F 0.32208(13) 0.68012(11) 0.53359(12) 0.0329(7) Uani 1.000000 . .
F9A F 0.38672(13) 0.75893(12) 0.36773(12) 0.0350(7) Uani 1.000000 . .
C22A C 0.16327(17) 0.70895(17) 0.46435(19) 0.0184(9) Uani 1.000000 . .
F13A F 0.41595(13) 0.85451(12) 0.70501(11) 0.0337(7) Uani 1.000000 . .
C13A C 0.39299(17) 0.81440(18) 0.62227(18) 0.0186(9) Uani 1.000000 . .
F15A F 0.39109(13) 0.76704(14) 0.70448(12) 0.0379(7) Uani 1.000000 . .
F14A F 0.47215(11) 0.79149(14) 0.67388(12) 0.0372(7) Uani 1.000000 . .
C5A C 0.3614(2) 0.88489(19) 0.3268(2) 0.0244(10) Uani 1.000000 . .
H5A H 0.3912(2) 0.87836(19) 0.3021(2) 0.0293(12) Uiso 1.000000 R .
C6A C 0.36006(18) 0.85488(18) 0.37489(18) 0.0201(10) Uani 1.000000 . .
C25A C 0.10555(19) 0.63674(17) 0.51098(19) 0.0199(9) Uani 1.000000 . .
C10A C 0.34684(17) 0.82498(17) 0.51811(17) 0.0147(9) Uani 1.000000 . .
C9A C 0.4059(2) 0.8103(2) 0.3816(2) 0.0288(11) Uani 1.000000 . .
F7A F 0.45152(12) 0.82116(14) 0.35214(14) 0.0431(8) Uani 1.000000 . .
F16A F 0.41045(13) 0.68845(12) 0.51660(13) 0.0375(8) Uani 1.000000 . .
C12A C 0.38227(19) 0.86702(19) 0.60088(19) 0.0218(9) Uani 1.000000 . .
H12A H 0.38903(19) 0.90019(19) 0.62149(19) 0.0261(11) Uiso 1.000000 R .
N1A N 0.12056(15) 0.66781(15) 0.46434(15) 0.0191(8) Uani 1.000000 . .
C35A C 0.0392(2) 0.6724(2) 0.3376(2) 0.0295(11) Uani 1.000000 . .
H35A H 0.0215(2) 0.6997(2) 0.3152(2) 0.0354(13) Uiso 1.000000 R .
C36A C 0.06550(19) 0.6899(2) 0.3840(2) 0.0250(10) Uani 1.000000 . .
H36A H 0.06474(19) 0.7289(2) 0.3938(2) 0.0300(13) Uiso 1.000000 R .
B1A B 0.3083(2) 0.8255(2) 0.4652(2) 0.0173(10) Uani 1.000000 . .
C26A C 0.1467(2) 0.61232(19) 0.54327(19) 0.0256(10) Uani 1.000000 . .
H26A H 0.1858(2) 0.61622(19) 0.53450(19) 0.0307(12) Uiso 1.000000 R .
C1A C 0.31730(18) 0.86253(18) 0.41271(18) 0.0179(9) Uani 1.000000 . .
C8A C 0.3206(2) 0.9579(2) 0.2643(2) 0.0325(12) Uani 1.000000 . .
C20A C 0.22770(18) 0.76921(19) 0.51264(18) 0.0197(9) Uani 1.000000 . .
H20A H 0.24109(18) 0.78306(19) 0.54581(18) 0.0236(11) Uiso 1.000000 R .
C32A C 0.09210(19) 0.5938(2) 0.4028(2) 0.0244(10) Uani 1.000000 . .
H32A H 0.11037(19) 0.5666(2) 0.4249(2) 0.0292(12) Uiso 1.000000 R .
C15A C 0.36244(17) 0.77171(18) 0.54074(18) 0.0180(9) Uani 1.000000 . .
F6A F 0.34201(17) 1.00886(13) 0.27128(14) 0.0533(9) Uani 1.000000 . .
C28A C 0.0755(3) 0.5756(2) 0.6003(2) 0.0393(13) Uani 1.000000 . .
H28A H 0.0650(3) 0.5545(2) 0.6310(2) 0.0471(16) Uiso 1.000000 R .
C18A C 0.3600(2) 0.71492(19) 0.5118(2) 0.0238(10) Uani 1.000000 . .
C33A C 0.0645(2) 0.5763(2) 0.3569(2) 0.0297(11) Uani 1.000000 . .
H33A H 0.0634(2) 0.5370(2) 0.3479(2) 0.0356(14) Uiso 1.000000 R .
C14A C 0.38458(18) 0.76644(18) 0.59121(18) 0.0183(9) Uani 1.000000 . .
H14A H 0.39408(18) 0.72991(18) 0.60470(18) 0.0219(11) Uiso 1.000000 R .
C27A C 0.1310(3) 0.5823(2) 0.5882(2) 0.0391(13) Uani 1.000000 . .
H27A H 0.1594(3) 0.5664(2) 0.6105(2) 0.0469(16) Uiso 1.000000 R .
F4A F 0.26697(16) 0.9666(2) 0.24595(15) 0.0707(13) Uani 1.000000 . .
C23A C 0.18819(18) 0.72749(19) 0.41730(18) 0.0208(9) Uani 1.000000 . .
H23A H 0.17460(18) 0.71341(19) 0.38429(18) 0.0249(11) Uiso 1.000000 R .
C24A C 0.23257(19) 0.76622(19) 0.41807(18) 0.0197(9) Uani 1.000000 . .
H24A H 0.24809(19) 0.77897(19) 0.38533(18) 0.0236(11) Uiso 1.000000 R .
C34A C 0.03837(19) 0.6163(2) 0.3239(2) 0.0281(11) Uani 1.000000 . .
H34A H 0.02015(19) 0.6045(2) 0.2921(2) 0.0337(13) Uiso 1.000000 R .
C19A C 0.25541(18) 0.78730(17) 0.46586(17) 0.0167(9) Uani 1.000000 . .
C30A C 0.0488(2) 0.63075(19) 0.5240(2) 0.0272(11) Uani 1.000000 . .
H30A H 0.0204(2) 0.64819(19) 0.5027(2) 0.0327(13) Uiso 1.000000 R .
C2A C 0.27512(19) 0.90376(18) 0.39888(18) 0.0200(9) Uani 1.000000 . .
F5A F 0.3490(2) 0.93170(16) 0.22715(14) 0.0690(13) Uani 1.000000 . .
C11A C 0.36168(17) 0.87231(17) 0.54956(18) 0.0176(9) Uani 1.000000 . .
C4A C 0.3194(2) 0.92387(18) 0.31564(19) 0.0240(10) Uani 1.000000 . .
C3A C 0.2763(2) 0.93400(18) 0.35186(19) 0.0252(10) Uani 1.000000 . .
H3A H 0.2478(2) 0.96154(18) 0.34446(19) 0.0302(12) Uiso 1.000000 R .
C31A C 0.09289(18) 0.65094(19) 0.41616(18) 0.0190(9) Uani 1.000000 . .
C21A C 0.18304(18) 0.73313(18) 0.51238(18) 0.0178(9) Uani 1.000000 . .
H21A H 0.16465(18) 0.72385(18) 0.54484(18) 0.0214(10) Uiso 1.000000 R .
C17A C 0.41803(19) 0.80729(19) 0.67647(19) 0.0214(10) Uani 1.000000 . .
C29A C 0.0335(3) 0.5993(2) 0.5682(2) 0.0392(13) Uani 1.000000 . .
H29A H -0.0056(3) 0.5940(2) 0.5766(2) 0.0470(16) Uiso 1.000000 R .
F10A F 0.30906(15) 0.95891(13) 0.54904(15) 0.0534(9) Uani 1.000000 . .
F12A F 0.39899(14) 0.96481(12) 0.55176(12) 0.0443(8) Uani 1.000000 . .
F11A F 0.35979(18) 0.93968(12) 0.47909(13) 0.0507(10) Uani 1.000000 . .
F3A F 0.21190(14) 0.97257(13) 0.43194(14) 0.0461(8) Uani 1.000000 . .
C16A C 0.3574(2) 0.93318(19) 0.5311(2) 0.0279(11) Uani 1.000000 . .
C7A C 0.2259(2) 0.9179(2) 0.4348(2) 0.0311(11) Uani 1.000000 . .
F1A F 0.23631(13) 0.90694(12) 0.48631(11) 0.0368(7) Uani 1.000000 . .
F2A F 0.17951(12) 0.88868(14) 0.42186(14) 0.0440(8) Uani 1.000000 . .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F18B C18B 1.326(5) .
F9B C9B 1.347(6) .
F17B C18B 1.340(5) .
F7B C9B 1.340(5) .
F8B C9B 1.332(6) .
F15B C17B 1.328(6) .
F13B C17B 1.336(6) .
C17B F14B 1.336(5) .
C17B C13B 1.506(7) .
N1B C31B 1.436(6) .
N1B C22B 1.394(6) .
N1B C25B 1.425(6) .
F16B C18B 1.351(5) .
F11B C16B 1.331(7) .
C4B C3B 1.368(8) .
C4B C5B 1.360(8) .
C4B C8B 1.492(8) .
C31B C36B 1.393(7) .
C31B C32B 1.385(7) .
F5B C8B 1.273(8) .
C34B C35B 1.378(7) .
C34B C33B 1.397(8) .
C10B B1B 1.595(7) .
C10B C15B 1.424(6) .
C10B C11B 1.432(6) .
C21B C22B 1.405(6) .
C21B C20B 1.388(7) .
F3B C7B 1.326(6) .
C24B C23B 1.359(7) .
C24B C19B 1.408(6) .
C1B C2B 1.401(6) .
C1B B1B 1.605(7) .
C1B C6B 1.410(6) .
C36B C35B 1.399(7) .
C12B C11B 1.401(7) .
C12B C13B 1.372(7) .
C22B C23B 1.409(6) .
C20B C19B 1.410(6) .
C14B C15B 1.383(7) .
C14B C13B 1.391(6) .
C2B C3B 1.409(7) .
C2B C7B 1.509(7) .
F6B C8B 1.273(7) .
C16B C11B 1.503(7) .
C16B F12B 1.300(6) .
C16B F10B 1.319(6) .
B1B C19B 1.541(7) .
C29B C30B 1.393(8) .
C29B C28B 1.365(9) .
C15B C18B 1.504(6) .
C33B C32B 1.382(7) .
F1B C7B 1.334(6) .
F4B C8B 1.289(8) .
C6B C5B 1.382(7) .
C6B C9B 1.520(7) .
C7B F2B 1.362(7) .
C30B C25B 1.386(7) .
C25B C26B 1.388(7) .
C28B C27B 1.380(9) .
C26B C27B 1.393(8) .
F18A C18A 1.324(5) .
F8A C9A 1.347(6) .
F17A C18A 1.329(6) .
F9A C9A 1.335(6) .
C22A N1A 1.394(5) .
C22A C23A 1.392(6) .
C22A C21A 1.415(6) .
F13A C17A 1.323(5) .
C13A C12A 1.372(6) .
C13A C14A 1.386(6) .
C13A C17A 1.496(6) .
F15A C17A 1.339(6) .
F14A C17A 1.327(5) .
C5A C6A 1.401(7) .
C5A C4A 1.377(7) .
C6A C9A 1.513(7) .
C6A C1A 1.396(6) .
C25A N1A 1.427(6) .
C25A C26A 1.388(6) .
C25A C30A 1.381(7) .
C10A B1A 1.612(7) .
C10A C15A 1.424(6) .
C10A C11A 1.409(6) .
C9A F7A 1.329(6) .
F16A C18A 1.345(5) .
C12A C11A 1.386(7) .
N1A C31A 1.433(6) .
C35A C36A 1.385(7) .
C35A C34A 1.363(7) .
C36A C31A 1.381(7) .
B1A C1A 1.596(7) .
B1A C19A 1.534(7) .
C26A C27A 1.383(7) .
C1A C2A 1.429(6) .
C8A F6A 1.311(6) .
C8A F4A 1.358(6) .
C8A F5A 1.302(6) .
C8A C4A 1.521(7) .
C20A C19A 1.412(6) .
C20A C21A 1.349(6) .
C32A C33A 1.387(7) .
C32A C31A 1.386(7) .
C15A C18A 1.522(6) .
C15A C14A 1.379(6) .
C28A C27A 1.348(8) .
C28A C29A 1.394(9) .
C33A C34A 1.398(8) .
C23A C24A 1.385(7) .
C24A C19A 1.408(6) .
C30A C29A 1.382(7) .
C2A C3A 1.381(7) .
C2A C7A 1.505(7) .
C11A C16A 1.508(6) .
C4A C3A 1.383(7) .
F10A C16A 1.364(6) .
F12A C16A 1.334(6) .
F11A C16A 1.319(6) .
F3A C7A 1.329(6) .
C7A F1A 1.345(6) .
C7A F2A 1.329(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
F13B C17B F15B 107.9(4) . .
F14B C17B F15B 105.7(4) . .
F14B C17B F13B 107.1(4) . .
C13B C17B F15B 113.0(4) . .
C13B C17B F13B 112.2(4) . .
C13B C17B F14B 110.6(4) . .
C22B N1B C31B 121.4(4) . .
C25B N1B C31B 116.6(4) . .
C25B N1B C22B 121.9(4) . .
C5B C4B C3B 120.8(5) . .
C8B C4B C3B 119.2(5) . .
C8B C4B C5B 119.9(5) . .
C36B C31B N1B 120.3(4) . .
C32B C31B N1B 119.5(4) . .
C32B C31B C36B 120.2(4) . .
C33B C34B C35B 119.6(5) . .
C15B C10B B1B 120.6(4) . .
C11B C10B B1B 124.1(4) . .
C11B C10B C15B 114.9(4) . .
C20B C21B C22B 119.7(4) . .
C19B C24B C23B 122.7(4) . .
B1B C1B C2B 119.3(4) . .
C6B C1B C2B 115.0(4) . .
C6B C1B B1B 125.7(4) . .
C35B C36B C31B 119.2(4) . .
C13B C12B C11B 120.3(4) . .
C21B C22B N1B 121.0(4) . .
C23B C22B N1B 121.0(4) . .
C23B C22B C21B 118.0(4) . .
C19B C20B C21B 122.8(4) . .
C13B C14B C15B 120.0(4) . .
C3B C2B C1B 121.9(5) . .
C7B C2B C1B 125.2(5) . .
C7B C2B C3B 112.9(4) . .
C22B C23B C24B 121.1(4) . .
C2B C3B C4B 119.5(5) . .
C11B C16B F11B 110.7(4) . .
F12B C16B F11B 106.2(4) . .
F12B C16B C11B 112.4(4) . .
F10B C16B F11B 104.2(4) . .
F10B C16B C11B 113.4(4) . .
F10B C16B F12B 109.3(4) . .
C1B B1B C10B 127.1(4) . .
C19B B1B C10B 117.2(4) . .
C19B B1B C1B 115.7(4) . .
C28B C29B C30B 120.7(5) . .
C14B C15B C10B 122.6(4) . .
C18B C15B C10B 124.5(4) . .
C18B C15B C14B 112.7(4) . .
C36B C35B C34B 120.5(5) . .
C20B C19B C24B 115.6(4) . .
B1B C19B C24B 122.7(4) . .
B1B C19B C20B 121.7(4) . .
C32B C33B C34B 120.1(5) . .
F17B C18B F18B 107.2(4) . .
F16B C18B F18B 105.3(4) . .
F16B C18B F17B 105.8(4) . .
C15B C18B F18B 115.8(4) . .
C15B C18B F17B 112.0(4) . .
C15B C18B F16B 110.1(4) . .
C5B C6B C1B 123.2(4) . .
C9B C6B C1B 120.3(4) . .
C9B C6B C5B 116.3(4) . .
C12B C11B C10B 121.6(4) . .
C16B C11B C10B 122.5(4) . .
C16B C11B C12B 115.8(4) . .
C6B C5B C4B 119.5(5) . .
C2B C7B F3B 112.2(5) . .
F1B C7B F3B 107.4(4) . .
F1B C7B C2B 115.3(4) . .
F2B C7B F3B 106.6(4) . .
F2B C7B C2B 109.9(4) . .
F2B C7B F1B 104.9(5) . .
C25B C30B C29B 119.8(5) . .
C30B C25B N1B 119.0(4) . .
C26B C25B N1B 121.1(4) . .
C26B C25B C30B 119.8(5) . .
C33B C32B C31B 120.2(4) . .
C12B C13B C17B 121.7(4) . .
C14B C13B C17B 118.0(4) . .
C14B C13B C12B 120.1(4) . .
F6B C8B F5B 107.0(7) . .
F4B C8B F5B 102.5(7) . .
F4B C8B F6B 102.5(6) . .
C27B C28B C29B 119.5(5) . .
C27B C26B C25B 119.1(5) . .
F7B C9B F9B 106.5(4) . .
F8B C9B F9B 106.9(4) . .
F8B C9B F7B 106.3(4) . .
C6B C9B F9B 111.0(4) . .
C6B C9B F7B 111.8(4) . .
C6B C9B F8B 113.9(4) . .
C26B C27B C28B 121.0(5) . .
C23A C22A N1A 121.3(4) . .
C21A C22A N1A 121.0(4) . .
C21A C22A C23A 117.7(4) . .
C14A C13A C12A 119.0(4) . .
C17A C13A C12A 122.1(4) . .
C17A C13A C14A 118.7(4) . .
C4A C5A C6A 119.7(4) . .
C9A C6A C5A 115.4(4) . .
C1A C6A C5A 122.8(4) . .
C1A C6A C9A 121.7(4) . .
C26A C25A N1A 121.4(4) . .
C30A C25A N1A 119.1(4) . .
C30A C25A C26A 119.4(4) . .
C15A C10A B1A 118.9(4) . .
C11A C10A B1A 126.7(4) . .
C11A C10A C15A 113.9(4) . .
F9A C9A F8A 107.3(4) . .
C6A C9A F8A 112.0(4) . .
C6A C9A F9A 110.9(4) . .
F7A C9A F8A 106.8(4) . .
F7A C9A F9A 107.4(4) . .
F7A C9A C6A 112.2(4) . .
C11A C12A C13A 120.7(4) . .
C25A N1A C22A 122.2(4) . .
C31A N1A C22A 121.3(4) . .
C31A N1A C25A 116.3(3) . .
C34A C35A C36A 120.4(5) . .
C31A C36A C35A 120.5(5) . .
C1A B1A C10A 127.9(4) . .
C19A B1A C10A 116.2(4) . .
C19A B1A C1A 115.8(4) . .
C27A C26A C25A 120.2(5) . .
B1A C1A C6A 126.2(4) . .
C2A C1A C6A 114.8(4) . .
C2A C1A B1A 118.6(4) . .
F4A C8A F6A 105.3(4) . .
F5A C8A F6A 109.4(5) . .
F5A C8A F4A 107.6(5) . .
C4A C8A F6A 111.9(4) . .
C4A C8A F4A 110.5(4) . .
C4A C8A F5A 111.8(4) . .
C21A C20A C19A 123.0(4) . .
C31A C32A C33A 119.7(5) . .
C18A C15A C10A 124.7(4) . .
C14A C15A C10A 123.0(4) . .
C14A C15A C18A 112.2(4) . .
C29A C28A C27A 120.4(5) . .
F17A C18A F18A 108.2(4) . .
F16A C18A F18A 105.8(4) . .
F16A C18A F17A 105.6(4) . .
C15A C18A F18A 115.9(4) . .
C15A C18A F17A 111.5(4) . .
C15A C18A F16A 109.2(4) . .
C34A C33A C32A 120.1(5) . .
C15A C14A C13A 120.1(4) . .
C28A C27A C26A 120.3(5) . .
C24A C23A C22A 120.7(4) . .
C19A C24A C23A 122.1(4) . .
C33A C34A C35A 119.7(5) . .
C20A C19A B1A 124.0(4) . .
C24A C19A B1A 120.4(4) . .
C24A C19A C20A 115.6(4) . .
C29A C30A C25A 119.8(5) . .
C3A C2A C1A 122.9(4) . .
C7A C2A C1A 122.4(4) . .
C7A C2A C3A 114.7(4) . .
C12A C11A C10A 122.7(4) . .
C16A C11A C10A 124.0(4) . .
C16A C11A C12A 113.4(4) . .
C8A C4A C5A 120.7(5) . .
C3A C4A C5A 120.3(4) . .
C3A C4A C8A 119.0(4) . .
C4A C3A C2A 119.5(4) . .
C36A C31A N1A 121.7(4) . .
C32A C31A N1A 118.7(4) . .
C32A C31A C36A 119.6(4) . .
C20A C21A C22A 120.8(4) . .
C13A C17A F13A 112.8(4) . .
F15A C17A F13A 106.8(4) . .
F15A C17A C13A 111.9(4) . .
F14A C17A F13A 107.3(4) . .
F14A C17A C13A 111.3(4) . .
F14A C17A F15A 106.4(4) . .
C30A C29A C28A 119.8(5) . .
F10A C16A C11A 112.0(4) . .
F12A C16A C11A 111.0(4) . .
F12A C16A F10A 103.5(4) . .
F11A C16A C11A 114.4(4) . .
F11A C16A F10A 108.3(4) . .
F11A C16A F12A 107.0(4) . .
F3A C7A C2A 111.8(4) . .
F1A C7A C2A 113.4(4) . .
F1A C7A F3A 106.4(4) . .
F2A C7A C2A 111.7(4) . .
F2A C7A F3A 106.4(4) . .
F2A C7A F1A 106.7(4) . .

_database_code_depnum_ccdc_archive 'CCDC 1010411'
#######################################################################
#
#                 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_lel006_0ma

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H9 B F18'
_chemical_formula_weight         650.12

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'
B B 0.0013 0.0007 '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           orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   15.5600(11)
_cell_length_b                   8.7136(6)
_cell_length_c                   35.624(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4830.1(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.788
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2560
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9609
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            67817
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4256
_reflns_number_gt                3188
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
The relatively high residual density of 0.9 is due to the disorder of the
CF3 group. 
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)+(0.0538P)²+4.7333P] 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         4256
_refine_ls_number_parameters     416
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1297
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.156
_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 0.54678(14) 0.69106(19) 0.07296(5) 0.0489(6) Uani 1 1 d . . .
F2 F 0.67726(13) 0.6538(2) 0.05580(6) 0.0484(5) Uani 1 1 d . . .
F3 F 0.57511(14) 0.64151(19) 0.01577(5) 0.0435(5) Uani 1 1 d . . .
F4 F 0.68172(14) -0.0358(2) 0.00618(6) 0.0515(6) Uani 1 1 d . . .
F5 F 0.59352(13) 0.0742(3) -0.03104(6) 0.0589(6) Uani 1 1 d . . .
F6 F 0.71688(13) 0.1712(2) -0.02173(6) 0.0506(6) Uani 1 1 d . . .
F7 F 0.49048(14) -0.04296(17) 0.10620(5) 0.0431(5) Uani 1 1 d . . .
F8 F 0.40474(11) 0.14645(19) 0.11387(5) 0.0363(5) Uani 1 1 d . . .
F9 F 0.51700(12) 0.12357(19) 0.14859(5) 0.0349(4) Uani 1 1 d . . .
F10 F 0.2614(13) 0.563(2) 0.0801(5) 0.033(4) Uani 0.377(18) 1 d P . .
F10A F 0.2687(9) 0.5773(15) 0.0820(3) 0.058(4) Uani 0.623(18) 1 d P . .
F11 F 0.3903(6) 0.4949(8) 0.0673(3) 0.024(2) Uani 0.377(18) 1 d P . .
F11A F 0.3716(7) 0.434(2) 0.0656(2) 0.093(4) Uani 0.623(18) 1 d P . .
F12 F 0.4084(7) 0.627(2) 0.0831(3) 0.064(5) Uani 0.377(18) 1 d P . .
F12A F 0.3723(5) 0.7026(6) 0.09550(14) 0.0418(18) Uani 0.623(18) 1 d P . .
F13 F 0.12459(14) 0.4416(4) 0.19051(7) 0.0909(10) Uani 1 1 d . . .
F14 F 0.19377(16) 0.4744(4) 0.23921(7) 0.0898(10) Uani 1 1 d . . .
F15 F 0.17634(17) 0.2533(3) 0.21974(10) 0.1105(13) Uani 1 1 d . . .
F16 F 0.51695(12) 0.4511(2) 0.23469(5) 0.0428(5) Uani 1 1 d . . .
F17 F 0.49326(11) 0.2114(2) 0.22626(5) 0.0379(5) Uani 1 1 d . . .
F18 F 0.58000(10) 0.33050(18) 0.19004(5) 0.0292(4) Uani 1 1 d . . .
B1 B 0.5214(2) 0.4596(3) 0.12529(9) 0.0210(7) Uani 1 1 d . . .
C1 C 0.54797(17) 0.3629(3) 0.08855(8) 0.0192(6) Uani 1 1 d . . .
C2 C 0.58820(17) 0.4331(3) 0.05724(8) 0.0212(6) Uani 1 1 d . . .
C3 C 0.62164(18) 0.3491(3) 0.02743(8) 0.0234(6) Uani 1 1 d . . .
H3A H 0.6481 0.4009 0.0070 0.028 Uiso 1 1 calc R . .
C4 C 0.61658(18) 0.1915(3) 0.02730(8) 0.0221(6) Uani 1 1 d . . .
C5 C 0.57318(18) 0.1175(3) 0.05594(8) 0.0232(6) Uani 1 1 d . . .
H5A H 0.5671 0.0090 0.0554 0.028 Uiso 1 1 calc R . .
C6 C 0.53849(17) 0.2010(3) 0.08540(8) 0.0197(6) Uani 1 1 d . . .
C7 C 0.5963(2) 0.6045(3) 0.05117(9) 0.0300(7) Uani 1 1 d . . .
C8 C 0.65216(19) 0.1008(3) -0.00472(9) 0.0290(7) Uani 1 1 d . . .
C9 C 0.4879(2) 0.1074(3) 0.11344(8) 0.0260(7) Uani 1 1 d . . .
C10 C 0.43168(17) 0.4386(3) 0.14683(7) 0.0181(6) Uani 1 1 d . . .
C11 C 0.35092(18) 0.4754(3) 0.13085(8) 0.0230(6) Uani 1 1 d . . .
C12 C 0.27397(18) 0.4600(3) 0.15017(8) 0.0265(7) Uani 1 1 d . . .
H12A H 0.2214 0.4877 0.1384 0.032 Uiso 1 1 calc R . .
C13 C 0.27382(17) 0.4045(3) 0.18641(8) 0.0227(6) Uani 1 1 d . . .
C14 C 0.35097(18) 0.3672(3) 0.20336(8) 0.0229(6) Uani 1 1 d . . .
H14A H 0.3512 0.3288 0.2283 0.028 Uiso 1 1 calc R . .
C15 C 0.42840(17) 0.3852(3) 0.18425(7) 0.0185(6) Uani 1 1 d . . .
C16 C 0.3447(2) 0.5471(4) 0.09258(10) 0.0411(9) Uani 1 1 d . . .
C17 C 0.19212(19) 0.3904(4) 0.20810(9) 0.0316(7) Uani 1 1 d . . .
C18 C 0.50544(18) 0.3448(3) 0.20812(8) 0.0231(6) Uani 1 1 d . . .
C19 C 0.58614(18) 0.5749(3) 0.14265(8) 0.0213(6) Uani 1 1 d . . .
C20 C 0.55764(19) 0.6934(3) 0.16615(8) 0.0258(7) Uani 1 1 d . . .
H20A H 0.4977 0.7059 0.1702 0.031 Uiso 1 1 calc R . .
C21 C 0.6144(2) 0.7929(3) 0.18362(9) 0.0329(7) Uani 1 1 d . . .
H21A H 0.5934 0.8750 0.1986 0.040 Uiso 1 1 calc R . .
C22 C 0.7021(2) 0.7717(4) 0.17910(9) 0.0364(8) Uani 1 1 d . . .
H22A H 0.7414 0.8377 0.1916 0.044 Uiso 1 1 calc R . .
C23 C 0.7323(2) 0.6548(4) 0.15645(9) 0.0359(8) Uani 1 1 d . . .
H23A H 0.7925 0.6399 0.1536 0.043 Uiso 1 1 calc R . .
C24 C 0.67527(19) 0.5591(3) 0.13785(8) 0.0276(7) Uani 1 1 d . . .
H24A H 0.6968 0.4817 0.1216 0.033 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C7 1.329(3) . ?
F2 C7 1.341(4) . ?
F3 C7 1.343(4) . ?
F4 C8 1.334(3) . ?
F5 C8 1.329(4) . ?
F6 C8 1.326(3) . ?
F7 C9 1.336(3) . ?
F8 C9 1.339(3) . ?
F9 C9 1.339(3) . ?
F10 C16 1.38(2) . ?
F10A C16 1.268(14) . ?
F11 F11A 0.607(18) . ?
F11 C16 1.233(12) . ?
F11 F12 1.31(2) . ?
F11A C16 1.437(12) . ?
F12 F12A 0.973(14) . ?
F12 C16 1.257(7) . ?
F12A C16 1.425(6) . ?
F13 C17 1.302(4) . ?
F14 C17 1.328(4) . ?
F15 C17 1.289(4) . ?
F16 C18 1.337(3) . ?
F17 C18 1.343(3) . ?
F18 C18 1.333(3) . ?
B1 C19 1.551(4) . ?
B1 C10 1.604(4) . ?
B1 C1 1.610(4) . ?
C1 C2 1.418(4) . ?
C1 C6 1.423(4) . ?
C2 C3 1.391(4) . ?
C2 C7 1.515(4) . ?
C3 C4 1.375(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.384(4) . ?
C4 C8 1.494(4) . ?
C5 C6 1.386(4) . ?
C5 H5A 0.9500 . ?
C6 C9 1.510(4) . ?
C10 C15 1.413(4) . ?
C10 C11 1.416(4) . ?
C11 C12 1.388(4) . ?
C11 C16 1.503(4) . ?
C12 C13 1.379(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.382(4) . ?
C13 C17 1.493(4) . ?
C14 C15 1.393(4) . ?
C14 H14A 0.9500 . ?
C15 C18 1.511(4) . ?
C19 C20 1.401(4) . ?
C19 C24 1.404(4) . ?
C20 C21 1.385(4) . ?
C20 H20A 0.9500 . ?
C21 C22 1.386(5) . ?
C21 H21A 0.9500 . ?
C22 C23 1.383(5) . ?
C22 H22A 0.9500 . ?
C23 C24 1.386(4) . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9500 . ?

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
F11A F11 C16 96.8(18) . . ?
F11A F11 F12 156(2) . . ?
C16 F11 F12 59.2(8) . . ?
F11 F11A C16 58.4(17) . . ?
F12A F12 C16 78.3(9) . . ?
F12A F12 F11 131.7(8) . . ?
C16 F12 F11 57.3(7) . . ?
F12 F12A C16 59.7(4) . . ?
C19 B1 C10 116.6(2) . . ?
C19 B1 C1 119.8(2) . . ?
C10 B1 C1 123.5(2) . . ?
C2 C1 C6 114.3(2) . . ?
C2 C1 B1 121.8(2) . . ?
C6 C1 B1 123.8(2) . . ?
C3 C2 C1 122.6(2) . . ?
C3 C2 C7 112.3(2) . . ?
C1 C2 C7 125.1(2) . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C5 119.4(3) . . ?
C3 C4 C8 120.7(3) . . ?
C5 C4 C8 119.8(2) . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C5 C6 C1 122.6(3) . . ?
C5 C6 C9 114.8(2) . . ?
C1 C6 C9 122.5(2) . . ?
F1 C7 F2 106.9(2) . . ?
F1 C7 F3 105.7(2) . . ?
F2 C7 F3 105.7(2) . . ?
F1 C7 C2 115.3(2) . . ?
F2 C7 C2 112.1(2) . . ?
F3 C7 C2 110.5(2) . . ?
F6 C8 F5 106.2(3) . . ?
F6 C8 F4 106.5(2) . . ?
F5 C8 F4 106.7(2) . . ?
F6 C8 C4 112.7(2) . . ?
F5 C8 C4 112.1(2) . . ?
F4 C8 C4 112.2(3) . . ?
F7 C9 F8 106.3(2) . . ?
F7 C9 F9 105.9(2) . . ?
F8 C9 F9 106.8(2) . . ?
F7 C9 C6 112.7(2) . . ?
F8 C9 C6 112.0(2) . . ?
F9 C9 C6 112.7(2) . . ?
C15 C10 C11 115.0(2) . . ?
C15 C10 B1 121.4(2) . . ?
C11 C10 B1 123.7(2) . . ?
C12 C11 C10 123.0(3) . . ?
C12 C11 C16 115.8(3) . . ?
C10 C11 C16 121.1(3) . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C12 C13 C14 119.3(3) . . ?
C12 C13 C17 121.0(3) . . ?
C14 C13 C17 119.6(3) . . ?
C13 C14 C15 120.8(3) . . ?
C13 C14 H14A 119.6 . . ?
C15 C14 H14A 119.6 . . ?
C14 C15 C10 122.0(2) . . ?
C14 C15 C18 112.6(2) . . ?
C10 C15 C18 125.4(2) . . ?
F11 C16 F12 63.5(11) . . ?
F11 C16 F10A 113.3(8) . . ?
F12 C16 F10A 122.7(9) . . ?
F11 C16 F10 110.1(8) . . ?
F12 C16 F10 127.0(10) . . ?
F10A C16 F10 6.4(14) . . ?
F11 C16 F12A 103.3(6) . . ?
F12 C16 F12A 41.9(7) . . ?
F10A C16 F12A 96.0(8) . . ?
F10 C16 F12A 102.3(9) . . ?
F11 C16 F11A 24.8(7) . . ?
F12 C16 F11A 88.2(16) . . ?
F10A C16 F11A 102.3(7) . . ?
F10 C16 F11A 97.3(8) . . ?
F12A C16 F11A 127.7(10) . . ?
F11 C16 C11 118.2(5) . . ?
F12 C16 C11 114.9(4) . . ?
F10A C16 C11 114.6(6) . . ?
F10 C16 C11 113.2(9) . . ?
F12A C16 C11 108.0(3) . . ?
F11A C16 C11 107.7(5) . . ?
F15 C17 F13 108.6(3) . . ?
F15 C17 F14 104.2(3) . . ?
F13 C17 F14 103.2(3) . . ?
F15 C17 C13 113.9(3) . . ?
F13 C17 C13 114.2(3) . . ?
F14 C17 C13 111.7(3) . . ?
F18 C18 F16 106.9(2) . . ?
F18 C18 F17 105.9(2) . . ?
F16 C18 F17 106.1(2) . . ?
F18 C18 C15 116.1(2) . . ?
F16 C18 C15 110.1(2) . . ?
F17 C18 C15 111.1(2) . . ?
C20 C19 C24 117.2(3) . . ?
C20 C19 B1 120.7(3) . . ?
C24 C19 B1 121.9(2) . . ?
C21 C20 C19 121.9(3) . . ?
C21 C20 H20A 119.1 . . ?
C19 C20 H20A 119.1 . . ?
C20 C21 C22 119.5(3) . . ?
C20 C21 H21A 120.3 . . ?
C22 C21 H21A 120.3 . . ?
C23 C22 C21 120.1(3) . . ?
C23 C22 H22A 120.0 . . ?
C21 C22 H22A 120.0 . . ?
C22 C23 C24 120.3(3) . . ?
C22 C23 H23A 119.9 . . ?
C24 C23 H23A 119.9 . . ?
C23 C24 C19 121.0(3) . . ?
C23 C24 H24A 119.5 . . ?
C19 C24 H24A 119.5 . . ?

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
F12 F11 F11A C16 9(4) . . . . ?
F11A F11 F12 F12A -37(6) . . . . ?
C16 F11 F12 F12A -26.8(10) . . . . ?
F11A F11 F12 C16 -10(5) . . . . ?
F11 F12 F12A C16 22.8(8) . . . . ?
C19 B1 C1 C2 -45.8(4) . . . . ?
C10 B1 C1 C2 137.1(3) . . . . ?
C19 B1 C1 C6 130.1(3) . . . . ?
C10 B1 C1 C6 -47.0(4) . . . . ?
C6 C1 C2 C3 -4.9(4) . . . . ?
B1 C1 C2 C3 171.4(3) . . . . ?
C6 C1 C2 C7 172.1(3) . . . . ?
B1 C1 C2 C7 -11.6(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C7 C2 C3 C4 -177.2(3) . . . . ?
C2 C3 C4 C5 4.0(4) . . . . ?
C2 C3 C4 C8 179.8(3) . . . . ?
C3 C4 C5 C6 -2.9(4) . . . . ?
C8 C4 C5 C6 -178.8(3) . . . . ?
C4 C5 C6 C1 -2.3(4) . . . . ?
C4 C5 C6 C9 176.2(3) . . . . ?
C2 C1 C6 C5 6.0(4) . . . . ?
B1 C1 C6 C5 -170.2(3) . . . . ?
C2 C1 C6 C9 -172.4(2) . . . . ?
B1 C1 C6 C9 11.3(4) . . . . ?
C3 C2 C7 F1 163.0(3) . . . . ?
C1 C2 C7 F1 -14.3(4) . . . . ?
C3 C2 C7 F2 -74.3(3) . . . . ?
C1 C2 C7 F2 108.4(3) . . . . ?
C3 C2 C7 F3 43.2(3) . . . . ?
C1 C2 C7 F3 -134.0(3) . . . . ?
C3 C4 C8 F6 28.1(4) . . . . ?
C5 C4 C8 F6 -156.1(3) . . . . ?
C3 C4 C8 F5 -91.7(3) . . . . ?
C5 C4 C8 F5 84.1(3) . . . . ?
C3 C4 C8 F4 148.3(3) . . . . ?
C5 C4 C8 F4 -35.9(4) . . . . ?
C5 C6 C9 F7 4.3(4) . . . . ?
C1 C6 C9 F7 -177.1(3) . . . . ?
C5 C6 C9 F8 -115.5(3) . . . . ?
C1 C6 C9 F8 63.1(3) . . . . ?
C5 C6 C9 F9 124.1(3) . . . . ?
C1 C6 C9 F9 -57.3(4) . . . . ?
C19 B1 C10 C15 -60.8(3) . . . . ?
C1 B1 C10 C15 116.4(3) . . . . ?
C19 B1 C10 C11 117.3(3) . . . . ?
C1 B1 C10 C11 -65.5(4) . . . . ?
C15 C10 C11 C12 -0.3(4) . . . . ?
B1 C10 C11 C12 -178.4(3) . . . . ?
C15 C10 C11 C16 174.4(3) . . . . ?
B1 C10 C11 C16 -3.8(4) . . . . ?
C10 C11 C12 C13 -1.0(4) . . . . ?
C16 C11 C12 C13 -175.9(3) . . . . ?
C11 C12 C13 C14 1.1(4) . . . . ?
C11 C12 C13 C17 178.5(3) . . . . ?
C12 C13 C14 C15 0.1(4) . . . . ?
C17 C13 C14 C15 -177.4(3) . . . . ?
C13 C14 C15 C10 -1.4(4) . . . . ?
C13 C14 C15 C18 177.5(2) . . . . ?
C11 C10 C15 C14 1.5(4) . . . . ?
B1 C10 C15 C14 179.7(2) . . . . ?
C11 C10 C15 C18 -177.3(2) . . . . ?
B1 C10 C15 C18 0.9(4) . . . . ?
F11A F11 C16 F12 176(2) . . . . ?
F11A F11 C16 F10A -68(2) . . . . ?
F12 F11 C16 F10A 116.3(9) . . . . ?
F11A F11 C16 F10 -62(2) . . . . ?
F12 F11 C16 F10 122.2(11) . . . . ?
F11A F11 C16 F12A -170.6(16) . . . . ?
F12 F11 C16 F12A 13.6(5) . . . . ?
F12 F11 C16 F11A -176(2) . . . . ?
F11A F11 C16 C11 70.3(19) . . . . ?
F12 F11 C16 C11 -105.5(6) . . . . ?
F12A F12 C16 F11 159.9(8) . . . . ?
F12A F12 C16 F10A 58.1(12) . . . . ?
F11 F12 C16 F10A -101.8(12) . . . . ?
F12A F12 C16 F10 63.9(13) . . . . ?
F11 F12 C16 F10 -96.0(13) . . . . ?
F11 F12 C16 F12A -159.9(8) . . . . ?
F12A F12 C16 F11A 161.7(6) . . . . ?
F11 F12 C16 F11A 1.8(8) . . . . ?
F12A F12 C16 C11 -89.6(6) . . . . ?
F11 F12 C16 C11 110.5(7) . . . . ?
F12 F12A C16 F11 -18.4(7) . . . . ?
F12 F12A C16 F10A -134.1(8) . . . . ?
F12 F12A C16 F10 -132.8(9) . . . . ?
F12 F12A C16 F11A -23.4(8) . . . . ?
F12 F12A C16 C11 107.6(5) . . . . ?
F11 F11A C16 F12 -3.8(18) . . . . ?
F11 F11A C16 F10A 119.4(19) . . . . ?
F11 F11A C16 F10 123(2) . . . . ?
F11 F11A C16 F12A 12(2) . . . . ?
F11 F11A C16 C11 -119.4(18) . . . . ?
C12 C11 C16 F11 -141.1(5) . . . . ?
C10 C11 C16 F11 43.9(6) . . . . ?
C12 C11 C16 F12 146.9(11) . . . . ?
C10 C11 C16 F12 -28.1(12) . . . . ?
C12 C11 C16 F10A -3.5(8) . . . . ?
C10 C11 C16 F10A -178.5(7) . . . . ?
C12 C11 C16 F10 -10.2(9) . . . . ?
C10 C11 C16 F10 174.7(8) . . . . ?
C12 C11 C16 F12A 102.2(5) . . . . ?
C10 C11 C16 F12A -72.8(5) . . . . ?
C12 C11 C16 F11A -116.6(7) . . . . ?
C10 C11 C16 F11A 68.4(7) . . . . ?
C12 C13 C17 F15 122.2(4) . . . . ?
C14 C13 C17 F15 -60.3(4) . . . . ?
C12 C13 C17 F13 -3.3(4) . . . . ?
C14 C13 C17 F13 174.1(3) . . . . ?
C12 C13 C17 F14 -120.0(3) . . . . ?
C14 C13 C17 F14 57.5(4) . . . . ?
C14 C15 C18 F18 167.6(2) . . . . ?
C10 C15 C18 F18 -13.6(4) . . . . ?
C14 C15 C18 F16 -70.9(3) . . . . ?
C10 C15 C18 F16 108.0(3) . . . . ?
C14 C15 C18 F17 46.4(3) . . . . ?
C10 C15 C18 F17 -134.7(3) . . . . ?
C10 B1 C19 C20 -23.3(4) . . . . ?
C1 B1 C19 C20 159.4(3) . . . . ?
C10 B1 C19 C24 152.0(3) . . . . ?
C1 B1 C19 C24 -25.3(4) . . . . ?
C24 C19 C20 C21 0.9(4) . . . . ?
B1 C19 C20 C21 176.5(3) . . . . ?
C19 C20 C21 C22 -2.7(4) . . . . ?
C20 C21 C22 C23 1.8(5) . . . . ?
C21 C22 C23 C24 0.7(5) . . . . ?
C22 C23 C24 C19 -2.4(5) . . . . ?
C20 C19 C24 C23 1.6(4) . . . . ?
B1 C19 C24 C23 -173.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.903
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.062
_database_code_depnum_ccdc_archive 'CCDC 1010412'
