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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_str1478
_audit_creation_date             2013-04-10
_audit_creation_method           
;
  Olex2 1.2-alpha
  (compiled Apr  9 2013 14:10:59, GUI svn.r4452)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C53 H72 N6, 3(B F4)'
_chemical_formula_sum            'C53 H72 B3 F12 N6'
_chemical_formula_weight         1053.60
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C53 H75 N6 B3 F12'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           185
_space_group_name_H-M_alt        'P 63 c m'
_space_group_name_Hall           'P 6c -2'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x-y, x, z+1/2'
3 'y, x, z'
4 '-y, x-y, z'
5 'x, x-y, z+1/2'
6 '-x+y, y, z+1/2'
7 '-x, -y, z+1/2'
8 'x-y, -y, z'
9 '-x, -x+y, z'
10 'y, -x+y, z+1/2'
11 '-x+y, -x, z'
12 '-y, -x, z+1/2'

_cell_length_a                   15.7431(5)
_cell_length_b                   15.7431(5)
_cell_length_c                   12.5624(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     2696.41(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4800
_cell_measurement_temperature    200.00(14)
_cell_measurement_theta_max      69.0500
_cell_measurement_theta_min      5.5960
_exptl_absorpt_coefficient_mu    0.886
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whitish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whitish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1110
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16021
_diffrn_reflns_theta_full        72.47
_diffrn_reflns_theta_max         72.47
_diffrn_reflns_theta_min         3.24
_diffrn_ambient_temperature      200.00(14)
_diffrn_detector_area_resol_mean 10.4051
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9991
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -117.00  -10.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -37.0000  -30.0000 107

#__ type_ start__ end____ width___ exp.time_
  2 omega  -45.00  -11.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      -68.5000   30.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
  3 omega   53.00   90.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308  -30.0000  -90.0000 37

#__ type_ start__ end____ width___ exp.time_
  4 omega   29.00   87.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308  -30.0000   60.0000 58

#__ type_ start__ end____ width___ exp.time_
  5 omega  103.00  172.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308  111.0000  150.0000 69

#__ type_ start__ end____ width___ exp.time_
  6 omega   46.00   96.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308  -45.0000    0.0000 50

#__ type_ start__ end____ width___ exp.time_
  7 omega   27.00   92.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308 -111.0000    0.0000 65

#__ type_ start__ end____ width___ exp.time_
  8 omega -116.00   -5.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -57.0000 -180.0000 111

#__ type_ start__ end____ width___ exp.time_
  9 omega   30.00  103.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -       37.6057 -136.0000 -145.0000 73

#__ type_ start__ end____ width___ exp.time_
 10 omega -147.00  -37.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      -68.5000  -45.0000  -90.0000 110

#__ type_ start__ end____ width___ exp.time_
 11 omega   30.00   98.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308  -45.0000  150.0000 68

#__ type_ start__ end____ width___ exp.time_
 12 omega   70.00  178.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308   30.0000 -180.0000 108

#__ type_ start__ end____ width___ exp.time_
 13 omega   27.00  115.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308 -111.0000 -180.0000 88

#__ type_ start__ end____ width___ exp.time_
 14 omega   27.00  178.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3308   15.0000   90.0000 151
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0844165000
_diffrn_orient_matrix_UB_12      -0.0952818000
_diffrn_orient_matrix_UB_13      -0.0472018000
_diffrn_orient_matrix_UB_21      -0.0349600000
_diffrn_orient_matrix_UB_22      -0.0399260000
_diffrn_orient_matrix_UB_23      0.1132595000
_diffrn_orient_matrix_UB_31      -0.0664392000
_diffrn_orient_matrix_UB_32      0.0458262000
_diffrn_orient_matrix_UB_33      0.0004159000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1704
_reflns_number_total             1899
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_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  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.682
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1899
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0696
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1620P)^2^+0.4171P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1947
_refine_ls_wR_factor_ref         0.2093
_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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. Others
 Fixed Sof: H5A(0.5) H5B(0.5) H5C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C13(H13)
3.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
N8 N 0.27357(17) 0.35434(16) 0.1959(2) 0.0530(6) Uani 1 1 d . . .
C7 C 0.21733(17) 0.26949(17) 0.2567(2) 0.0472(6) Uani 1 1 d . . .
C6 C 0.12818(18) 0.23313(18) 0.3089(3) 0.0494(6) Uani 1 1 d . . .
H6 H 0.0939 0.2671 0.3093 0.059 Uiso 1 1 calc R . .
C2 C 0.09264(16) 0.14422(18) 0.36024(19) 0.0449(6) Uani 1 1 d . . .
C9 C 0.2503(2) 0.4351(2) 0.1754(3) 0.0618(8) Uani 1 1 d . . .
C10 C 0.3299(3) 0.5113(3) 0.1047(4) 0.0826(11) Uani 1 1 d . . .
H10A H 0.3920 0.5386 0.1405 0.124 Uiso 1 1 calc R . .
H10B H 0.3155 0.5625 0.0894 0.124 Uiso 1 1 calc R . .
H10C H 0.3327 0.4811 0.0394 0.124 Uiso 1 1 calc R . .
C11 C 0.1528(3) 0.3910(3) 0.1149(4) 0.0729(9) Uani 1 1 d . . .
H11A H 0.1594 0.3664 0.0474 0.109 Uiso 1 1 calc R . .
H11B H 0.1354 0.4407 0.1038 0.109 Uiso 1 1 calc R . .
H11C H 0.1024 0.3384 0.1558 0.109 Uiso 1 1 calc R . .
F16 F 0.5564(5) 0.4728(4) 0.3844(7) 0.217(4) Uani 1 1 d . . .
C12 C 0.2472(3) 0.4791(2) 0.2813(4) 0.0784(11) Uani 1 1 d . . .
H12A H 0.1992 0.4288 0.3264 0.118 Uiso 1 1 calc R . .
H12B H 0.2299 0.5290 0.2701 0.118 Uiso 1 1 calc R . .
H12C H 0.3104 0.5076 0.3146 0.118 Uiso 1 1 calc R . .
F14 F 0.6358(2) 0.6358(2) 0.3723(5) 0.127(2) Uani 1 2 d S . .
C3 C 0.0000 0.0000 0.4745(5) 0.0473(13) Uani 1 6 d S . .
C1 C 0.0000 0.0936(2) 0.4271(3) 0.0470(8) Uani 1 2 d S . .
C5 C 0.0000 0.1661(3) 0.5087(4) 0.0601(10) Uani 1 2 d S . .
H5A H 0.0531 0.1847 0.5579 0.090 Uiso 0.50 1 calc PR A -1
H5B H -0.0611 0.1356 0.5467 0.090 Uiso 0.50 1 calc PR A -1
H5C H 0.0080 0.2233 0.4725 0.090 Uiso 0.50 1 calc PR A -1
C13 C 0.3530(2) 0.3530(2) 0.1634(4) 0.0552(9) Uani 1 2 d S . .
H13 H 0.4022 0.4022 0.1224 0.066 Uiso 1 2 calc SR . .
F17 F 0.5358(4) 0.5358(4) 0.2476(6) 0.161(2) Uani 1 2 d S . .
B15 B 0.5499(4) 0.5499(4) 0.3527(7) 0.0805(16) Uani 1 2 d S . .
C4 C 0.0000 0.0000 0.5982(7) 0.0649(17) Uani 1 6 d S . .

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
N8 0.0368(10) 0.0346(11) 0.0847(16) 0.0013(11) 0.0001(10) 0.0156(8)
C7 0.0348(11) 0.0313(11) 0.0715(14) -0.0028(10) -0.0059(11) 0.0134(9)
C6 0.0359(12) 0.0347(12) 0.0772(15) -0.0059(11) -0.0047(12) 0.0174(10)
C2 0.0335(11) 0.0357(11) 0.0624(13) -0.0040(10) -0.0021(10) 0.0149(9)
C9 0.0502(14) 0.0371(13) 0.098(2) 0.0035(13) 0.0001(15) 0.0217(11)
C10 0.064(2) 0.0477(16) 0.135(3) 0.016(2) 0.015(2) 0.0267(15)
C11 0.0615(18) 0.0570(18) 0.108(3) 0.0051(18) -0.0041(18) 0.0356(15)
F16 0.175(5) 0.099(3) 0.349(10) 0.030(4) -0.090(6) 0.048(3)
C12 0.076(2) 0.0479(16) 0.114(3) -0.0056(16) -0.0010(19) 0.0335(16)
F14 0.0754(16) 0.0754(16) 0.221(6) -0.048(2) -0.048(2) 0.0313(18)
C3 0.0409(17) 0.0409(17) 0.060(3) 0.000 0.000 0.0204(8)
C1 0.0369(18) 0.0379(13) 0.066(2) -0.0046(12) 0.000 0.0185(9)
C5 0.057(2) 0.0519(15) 0.073(2) -0.0105(16) 0.000 0.0286(11)
C13 0.0389(13) 0.0389(13) 0.080(2) 0.0007(14) 0.0007(14) 0.0139(15)
F17 0.143(3) 0.143(3) 0.162(5) -0.053(3) -0.053(3) 0.046(4)
B15 0.071(3) 0.071(3) 0.104(4) -0.010(3) -0.010(3) 0.038(3)
C4 0.062(2) 0.062(2) 0.070(4) 0.000 0.000 0.0311(12)

_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
N8 C7 1.403(3) . ?
N8 C9 1.511(4) . ?
N8 C13 1.326(3) . ?
C7 C7 1.422(5) 3 ?
C7 C6 1.387(4) . ?
C6 C2 1.380(4) . ?
C2 C2 1.406(5) 3 ?
C2 C1 1.519(3) . ?
C9 C10 1.515(5) . ?
C9 C11 1.533(5) . ?
C9 C12 1.513(6) . ?
F16 B15 1.328(6) . ?
F14 B15 1.373(8) . ?
C3 C1 1.589(5) . ?
C3 C1 1.589(5) 3 ?
C3 C1 1.589(5) 4 ?
C3 C4 1.553(11) . ?
C1 C2 1.519(3) 9 ?
C1 C5 1.534(5) . ?
C13 N8 1.326(3) 3 ?
F17 B15 1.340(10) . ?
B15 F16 1.328(6) 3 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N8 C9 126.2(2) . . ?
C13 N8 C7 107.7(2) . . ?
C13 N8 C9 126.0(3) . . ?
N8 C7 C7 106.14(13) . 3 ?
C6 C7 N8 132.6(2) . . ?
C6 C7 C7 121.26(15) . 3 ?
C2 C6 C7 116.9(2) . . ?
C6 C2 C2 121.82(15) . 3 ?
C6 C2 C1 125.9(3) . . ?
C2 C2 C1 112.15(17) 3 . ?
N8 C9 C10 108.3(3) . . ?
N8 C9 C11 108.3(2) . . ?
N8 C9 C12 108.2(3) . . ?
C10 C9 C11 108.2(3) . . ?
C12 C9 C10 110.9(3) . . ?
C12 C9 C11 112.8(3) . . ?
C1 C3 C1 106.8(3) 4 3 ?
C1 C3 C1 106.8(3) 4 . ?
C1 C3 C1 106.8(3) 3 . ?
C4 C3 C1 112.0(3) . . ?
C4 C3 C1 112.0(3) . 3 ?
C4 C3 C1 112.0(3) . 4 ?
C2 C1 C2 112.6(3) 9 . ?
C2 C1 C3 104.4(2) . . ?
C2 C1 C3 104.4(2) 9 . ?
C2 C1 C5 109.6(2) . . ?
C2 C1 C5 109.6(2) 9 . ?
C5 C1 C3 116.1(4) . . ?
N8 C13 N8 112.3(3) . 3 ?
F16 B15 F16 118.0(9) . 3 ?
F16 B15 F14 111.0(4) 3 . ?
F16 B15 F14 111.0(4) . . ?
F16 B15 F17 103.0(5) . . ?
F16 B15 F17 103.0(5) 3 . ?
F17 B15 F14 109.9(7) . . ?

_database_code_depnum_ccdc_archive 'CCDC 950746'