# Supplementary Material (ESI) for ChemComm
# This journal is © The Royal Society of Chemistry 1999
# CCDC Number: 182/1475



###################################################
# CIF begins here
# Provided by W.Clegg@ncl.ac.uk

data_tbm45

_audit_creation_method            SHELXL
_chemical_name_systematic
;
  ?
;
_chemical_name_common             ?
_chemical_formula_moiety          ?
_chemical_formula_structural      ?
_chemical_formula_analytical      ?
_chemical_formula_sum             'C44 H14 F14'
_chemical_formula_weight          808.55
_chemical_melting_point           ?
_chemical_compound_source         ?

loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
  'C'  'C'   0.0033   0.0016
  'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
  'H'  'H'   0.0000   0.0000
  'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
  'F'  'F'   0.0171   0.0103
  'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting            triclinic
_symmetry_space_group_name_H-M    P-1

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

_cell_length_a                    6.0932(7)
_cell_length_b                    7.5393(9)
_cell_length_c                    19.114(2)
_cell_angle_alpha                 96.044(3)
_cell_angle_beta                  99.102(3)
_cell_angle_gamma                 96.538(3)
_cell_volume                      854.54(17)
_cell_formula_units_Z             1
_cell_measurement_temperature     160(2)
_cell_measurement_reflns_used     2327
_cell_measurement_theta_min       2.17
_cell_measurement_theta_max       27.88

_exptl_crystal_description        Plate
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.62
_exptl_crystal_size_mid           0.18
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.571
_exptl_crystal_density_method     ?
_exptl_crystal_F_000              404
_exptl_absorpt_coefficient_mu     0.145
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?

_exptl_special_details
;
  ?
;

_diffrn_ambient_temperature       160(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        'Siemens SMART CCD diffractometer'
_diffrn_measurement_method        '\w rotation with narrow frames'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             4436
_diffrn_reflns_av_R_equivalents   0.0449
_diffrn_reflns_av_sigmaI/netI     0.0355
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        4
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -24
_diffrn_reflns_limit_l_max        25
_diffrn_reflns_theta_min          1.09
_diffrn_reflns_theta_max          25.00
_reflns_number_total              2918
_reflns_number_observed           2217
_reflns_observed_criterion        >2sigma(I)

_computing_data_collection        'Siemens SMART'
_computing_cell_refinement        'local programs'
_computing_data_reduction         'Siemens SAINT'
_computing_structure_solution     'SHELXS-96 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-96 (Sheldrick, 1996)'
_computing_molecular_graphics     ?
_computing_publication_material   ?

_refine_special_details
;
  Refinement of F^2^ against ALL reflections.  Weighted R-factors wR and 
all
  goodnesses of fit S are based on F^2^, conventional R-factors R
  are based on F, with F set to zero for negative F^2^. The observed 
criterion
  of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. 
and is
  not relevant to the choice of reflections for refinement.  R-factors 
based
  on F^2^ are statistically about twice as large as those based on F, 
and R-
  factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme
  'calc w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+1.5407P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     ?
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.0034(11)
_refine_ls_extinction_expression
  'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_number_reflns          2918
_refine_ls_number_parameters      263
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0931
_refine_ls_R_factor_obs           0.0685
_refine_ls_wR_factor_all          0.1661
_refine_ls_wR_factor_obs          0.1442
_refine_ls_goodness_of_fit_all    1.239
_refine_ls_goodness_of_fit_obs    1.251
_refine_ls_restrained_S_all       1.239
_refine_ls_restrained_S_obs       1.251
_refine_ls_shift/esd_max          0.000
_refine_ls_shift/esd_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_thermal_displace_type
  _atom_site_occupancy
  _atom_site_calc_flag
  _atom_site_refinement_flags
  _atom_site_disorder_group
C1 C 0.3876(7) 0.5829(5) -0.4105(2) 0.0364(9) Uani 1 d . .
H1 H 0.3185 0.5881 -0.4582 0.044 Uiso 1 calc R .
C2 C 0.6136(7) 0.6448(5) -0.3884(2) 0.0345(9) Uani 1 d . .
H2 H 0.6991 0.6930 -0.4211 0.041 Uiso 1 calc R .
C3 C 0.7154(6) 0.6369(5) -0.31904(19) 0.0295(8) Uani 1 d . .
H3 H 0.8700 0.6810 -0.3041 0.035 Uiso 1 calc R .
C4 C 0.5912(6) 0.5642(4) -0.27075(18) 0.0256(8) Uani 1 d . .
C5 C 0.3629(6) 0.5047(5) -0.29294(19) 0.0291(8) Uani 1 d . .
H5 H 0.2762 0.4581 -0.2602 0.035 Uiso 1 calc R .
C6 C 0.2623(6) 0.5132(5) -0.3624(2) 0.0357(9) Uani 1 d . .
H6 H 0.1071 0.4713 -0.3773 0.043 Uiso 1 calc R .
C7 C 0.6989(6) 0.5492(5) -0.20004(19) 0.0275(8) Uani 1 d . .
C8 C 0.7910(6) 0.5304(4) -0.14101(18) 0.0265(8) Uani 1 d . .
C9 C 0.8962(6) 0.5131(4) -0.07110(18) 0.0248(7) Uani 1 d . .
C10 C 0.7801(5) 0.4311(4) -0.02307(19) 0.0250(8) Uani 1 d . .
C11 C 0.8786(6) 0.4201(4) 0.04535(18) 0.0244(7) Uani 1 d . .
F1 F 0.5640(3) 0.3614(3) -0.04534(11) 0.0326(5) Uani 1 d . .
F2 F 0.7561(3) 0.3410(3) 0.08909(11) 0.0346(5) Uani 1 d . .
C12 C 0.6033(6) 0.9100(5) 0.40936(17) 0.0270(8) Uani 1 d . .
F3 F 0.6966(4) 0.8964(3) 0.47681(11) 0.0429(6) Uani 1 d . .
C13 C 0.7290(5) 0.9912(5) 0.36494(19) 0.0267(8) Uani 1 d . .
F4 F 0.9445(3) 1.0584(3) 0.38986(12) 0.0402(6) Uani 1 d . .
C14 C 0.6348(6) 1.0021(4) 0.29585(19) 0.0266(8) Uani 1 d . .
F5 F 0.7611(3) 1.0800(3) 0.25338(11) 0.0363(5) Uani 1 d . .
C15 C 0.4115(5) 0.9352(4) 0.26871(17) 0.0232(7) Uani 1 d . .
C16 C 0.2890(6) 0.8546(5) 0.31550(18) 0.0258(8) Uani 1 d . .
F6 F 0.0734(3) 0.7864(3) 0.29225(11) 0.0352(5) Uani 1 d . .
C17 C 0.3820(6) 0.8419(5) 0.38449(18) 0.0272(8) Uani 1 d . .
F7 F 0.2584(4) 0.7638(3) 0.42842(11) 0.0386(6) Uani 1 d . .
C18 C 0.3086(6) 0.9537(5) 0.19826(18) 0.0271(8) Uani 1 d . .
C19 C 0.2173(6) 0.9716(4) 0.13974(18) 0.0254(8) Uani 1 d . .
C20 C 0.1064(5) 0.9878(4) 0.06920(17) 0.0219(7) Uani 1 d . .
C21 C -0.1226(6) 0.9245(5) 0.04776(18) 0.0274(8) Uani 1 d . .
H21 H -0.2055 0.8729 0.0804 0.033 Uiso 1 calc R .
C22 C 0.2272(6) 1.0628(4) 0.02036(18) 0.0253(7) Uani 1 d . .
H22 H 0.3825 1.1051 0.0345 0.030 Uiso 1 calc R .

loop_
  _atom_site_aniso_label
  _atom_site_aniso_U_11
  _atom_site_aniso_U_22
  _atom_site_aniso_U_33
  _atom_site_aniso_U_23
  _atom_site_aniso_U_13
  _atom_site_aniso_U_12
C1 0.055(3) 0.030(2) 0.0245(19) 0.0042(15) 0.0022(17) 0.0106(18)
C2 0.047(2) 0.029(2) 0.030(2) 0.0075(15) 0.0144(17) 0.0036(17)
C3 0.0284(19) 0.0241(19) 0.035(2) 0.0023(15) 0.0074(15) -0.0025(14)
C4 0.0317(19) 0.0189(17) 0.0248(18) -0.0003(13) 0.0039(14) 0.0022(14)
C5 0.0268(18) 0.030(2) 0.031(2) 0.0045(15) 0.0098(15) 0.0009(15)
C6 0.031(2) 0.034(2) 0.039(2) 0.0005(16) 0.0012(16) 0.0023(16)
C7 0.0277(19) 0.0208(18) 0.034(2) 0.0029(15) 0.0099(16) -0.0011(14)
C8 0.0287(18) 0.0199(18) 0.030(2) 0.0034(14) 0.0059(15) -0.0026(14)
C9 0.0256(18) 0.0207(18) 0.0282(18) 0.0018(14) 0.0057(14) 0.0033(13)
C10 0.0237(17) 0.0198(18) 0.0311(19) 0.0005(14) 0.0072(14) 0.0002(14)
C11 0.0244(17) 0.0209(18) 0.0298(19) 0.0038(14) 0.0106(14) 0.0019(13)
F1 0.0211(10) 0.0340(12) 0.0389(12) 0.0014(9) 0.0030(9) -0.0064(8)
F2 0.0325(12) 0.0377(12) 0.0345(12) 0.0084(9) 0.0141(9) -0.0063(9)
C12 0.037(2) 0.0251(19) 0.0182(17) 0.0005(13) 0.0006(14) 0.0083(15)
F3 0.0557(15) 0.0457(14) 0.0245(11) 0.0035(10) -0.0005(10) 0.0062(11)
C13 0.0193(17) 0.0277(19) 0.0310(19) -0.0006(14) 0.0008(14) 0.0029(14)
F4 0.0259(11) 0.0456(14) 0.0435(13) -0.0010(10) -0.0022(9) -0.0019(9)
C14 0.0308(19) 0.0198(18) 0.0301(19) 0.0052(14) 0.0098(15) -0.0004(14)
F5 0.0355(12) 0.0390(13) 0.0355(12) 0.0103(9) 0.0131(9) -0.0050(9)
C15 0.0251(17) 0.0187(17) 0.0252(18) 0.0014(13) 0.0043(14) 0.0018(13)
C16 0.0241(18) 0.0225(18) 0.0295(19) 0.0016(14) 0.0021(14) 0.0027(14)
F6 0.0264(11) 0.0383(13) 0.0380(12) 0.0020(9) 0.0053(9) -0.0045(9)
C17 0.038(2) 0.0221(18) 0.0249(18) 0.0060(14) 0.0141(15) 0.0024(15)
F7 0.0505(14) 0.0373(13) 0.0305(12) 0.0095(9) 0.0167(10) -0.0018(10)
C18 0.0311(19) 0.0240(19) 0.0251(19) 0.0004(14) 0.0072(15) -0.0012(14)
C19 0.0278(18) 0.0199(18) 0.028(2) 0.0008(14) 0.0067(15) 0.0016(14)
C20 0.0255(18) 0.0197(17) 0.0202(17) 0.0033(13) 0.0031(13) 0.0024(13)
C21 0.0287(19) 0.0241(19) 0.0287(19) 0.0037(14) 0.0077(14) -0.0030(14)
C22 0.0224(17) 0.0232(18) 0.0295(19) 0.0014(14) 0.0049(14) 0.0002(14)

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

loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
C1 C2 1.3858(56) . ?
C1 C6 1.3917(56) . ?
C2 C3 1.3820(51) . ?
C3 C4 1.3995(48) . ?
C4 C5 1.3955(48) . ?
C4 C7 1.4279(48) . ?
C5 C6 1.3822(52) . ?
C7 C8 1.2081(49) . ?
C8 C9 1.4134(48) . ?
C9 C10 1.3966(47) . ?
C9 C11 1.3987(46) 2_765 ?
C10 F1 1.3449(38) . ?
C10 C11 1.3651(48) . ?
C11 F2 1.3463(38) . ?
C11 C9 1.3987(46) 2_765 ?
C12 F3 1.3437(38) . ?
C12 C13 1.3746(50) . ?
C12 C17 1.3773(50) . ?
C13 F4 1.3445(38) . ?
C13 C14 1.3688(49) . ?
C14 F5 1.3383(38) . ?
C14 C15 1.3931(47) . ?
C15 C16 1.3961(47) . ?
C15 C18 1.4206(47) . ?
C16 F6 1.3419(38) . ?
C16 C17 1.3682(48) . ?
C17 F7 1.3493(38) . ?
C18 C19 1.1959(48) . ?
C19 C20 1.4335(46) . ?
C20 C22 1.4024(46) . ?
C20 C21 1.4033(46) . ?
C21 C22 1.3740(48) 2_575 ?
C22 C21 1.3740(48) 2_575 ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
C2 C1 C6 119.8(4) . . ?
C3 C2 C1 120.4(3) . . ?
C2 C3 C4 120.1(3) . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 C7 120.8(3) . . ?
C3 C4 C7 120.0(3) . . ?
C6 C5 C4 120.3(3) . . ?
C5 C6 C1 120.2(4) . . ?
C8 C7 C4 177.7(4) . . ?
C7 C8 C9 178.3(4) . . ?
C10 C9 C11 115.9(3) . 2_765 ?
C10 C9 C8 121.9(3) . . ?
C11 C9 C8 122.1(3) 2_765 . ?
F1 C10 C11 119.3(3) . . ?
F1 C10 C9 118.5(3) . . ?
C11 C10 C9 122.2(3) . . ?
F2 C11 C10 119.1(3) . . ?
F2 C11 C9 119.0(3) . 2_765 ?
C10 C11 C9 121.9(3) . 2_765 ?
F3 C12 C13 120.0(3) . . ?
F3 C12 C17 120.1(3) . . ?
C13 C12 C17 119.9(3) . . ?
F4 C13 C14 120.6(3) . . ?
F4 C13 C12 119.4(3) . . ?
C14 C13 C12 120.0(3) . . ?
F5 C14 C13 118.9(3) . . ?
F5 C14 C15 119.2(3) . . ?
C13 C14 C15 121.9(3) . . ?
C14 C15 C16 116.5(3) . . ?
C14 C15 C18 122.5(3) . . ?
C16 C15 C18 121.0(3) . . ?
F6 C16 C17 118.7(3) . . ?
F6 C16 C15 119.2(3) . . ?
C17 C16 C15 122.1(3) . . ?
F7 C17 C16 120.6(3) . . ?
F7 C17 C12 119.8(3) . . ?
C16 C17 C12 119.7(3) . . ?
C19 C18 C15 178.2(4) . . ?
C18 C19 C20 178.5(4) . . ?
C22 C20 C21 119.4(3) . . ?
C22 C20 C19 120.3(3) . . ?
C21 C20 C19 120.3(3) . . ?
C22 C21 C20 120.1(3) 2_575 . ?
C21 C22 C20 120.5(3) 2_575 . ?

_refine_diff_density_max    0.295
_refine_diff_density_min   -0.302
_refine_diff_density_rms    0.064