# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2007

data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Prof. Nicholas Norman'
_publ_contact_author_email       N.C.NORMAN@BRISTOL.AC.UK
loop_
_publ_author_name
N.Norman
'George Bramham'
'Jonathan Charmant'
'Alistair J.R. Cook'
C.Russell
'Saowanit Saithong'

data_g63-fdd2
_database_code_depnum_ccdc_archive 'CCDC 655805'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H52 B8 N12'
_chemical_formula_sum            'C16 H52 B8 N12'
_chemical_formula_weight         499.18

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'F d d 2 '
_symmetry_space_group_name_Hall  'F 2 -2d'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   22.220(4)
_cell_length_b                   28.467(6)
_cell_length_c                   9.5966(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6070(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2522
_cell_measurement_theta_min      2.3255
_cell_measurement_theta_max      26.3825

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.121
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.092
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2176
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.192
_diffrn_detector_type            'Bruker-AXS SMART 1k'
_diffrn_measurement_details      'frames, 0.3\% width'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker-AXS Platform'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'glass fibre'
_diffrn_radiation_collimation    '0.5 mm double pin hole'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71074
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           40
_diffrn_source_power             2
_diffrn_source_target            Mo
_diffrn_source_voltage           50
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16769
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1847
_reflns_number_gt                1777
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART v5.628 (Bruker-AXS, 1997-2002)'
_computing_cell_refinement       'SMART v5.628 (Bruker-AXS, 1997-2002)'
_computing_data_reduction        
;
SAINT v7.06A (Bruker-AXS, 1997-2003) & SHELXTL v6.14 (Bruker-AXS, 2003)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0607P)^2^+8.8564P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         1847
_refine_ls_number_parameters     177
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1256
_refine_ls_wR_factor_gt          0.1246
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_restrained_S_all      1.180
_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
N1 N 0.43986(10) 0.03547(8) 0.4902(2) 0.0151(5) Uani 1 1 d . . .
N2 N 0.54563(10) 0.04846(7) 0.7842(2) 0.0138(4) Uani 1 1 d . . .
N3 N 0.34733(10) -0.01115(8) 0.5171(3) 0.0182(5) Uani 1 1 d . . .
N4 N 0.52626(10) 0.08532(7) 0.4220(2) 0.0161(5) Uani 1 1 d . . .
N5 N 0.47713(10) 0.11638(7) 0.7593(2) 0.0165(5) Uani 1 1 d . . .
N6 N 0.60956(10) -0.01766(8) 0.8567(2) 0.0148(5) Uani 1 1 d . . .
B1 B 0.40182(14) 0.00641(9) 0.5751(3) 0.0130(6) Uani 1 1 d . . .
B2 B 0.49103(13) 0.06376(10) 0.5281(3) 0.0134(5) Uani 1 1 d . . .
B3 B 0.50585(12) 0.07644(9) 0.6998(3) 0.0120(5) Uani 1 1 d . . .
B4 B 0.58206(12) 0.00806(10) 0.7471(3) 0.0129(6) Uani 1 1 d . . .
C1 C 0.30501(13) -0.03944(11) 0.5945(4) 0.0246(6) Uani 1 1 d . . .
H1A H 0.3205 -0.0448 0.6888 0.037 Uiso 1 1 calc R . .
H1B H 0.2995 -0.0697 0.5473 0.037 Uiso 1 1 calc R . .
H1C H 0.2663 -0.0230 0.6001 0.037 Uiso 1 1 calc R . .
C2 C 0.32612(13) -0.00129(11) 0.3767(3) 0.0249(6) Uani 1 1 d . . .
H2A H 0.3542 0.0202 0.3305 0.037 Uiso 1 1 calc R . .
H2B H 0.2862 0.0132 0.3813 0.037 Uiso 1 1 calc R . .
H2C H 0.3237 -0.0307 0.3237 0.037 Uiso 1 1 calc R . .
C3 C 0.51923(15) 0.07704(11) 0.2742(3) 0.0252(6) Uani 1 1 d . . .
H3A H 0.4949 0.0488 0.2597 0.038 Uiso 1 1 calc R . .
H3B H 0.5589 0.0727 0.2315 0.038 Uiso 1 1 calc R . .
H3C H 0.4992 0.1041 0.2313 0.038 Uiso 1 1 calc R . .
C4 C 0.57485(13) 0.11792(10) 0.4522(3) 0.0227(6) Uani 1 1 d . . .
H4A H 0.5798 0.1207 0.5533 0.034 Uiso 1 1 calc R . .
H4B H 0.5652 0.1488 0.4129 0.034 Uiso 1 1 calc R . .
H4C H 0.6123 0.1062 0.4107 0.034 Uiso 1 1 calc R . .
C5 C 0.43625(13) 0.14621(9) 0.6820(3) 0.0217(6) Uani 1 1 d . . .
H5A H 0.4301 0.1331 0.5886 0.033 Uiso 1 1 calc R . .
H5B H 0.4534 0.1778 0.6742 0.033 Uiso 1 1 calc R . .
H5C H 0.3976 0.1479 0.7309 0.033 Uiso 1 1 calc R . .
C6 C 0.48514(13) 0.13319(10) 0.8995(3) 0.0232(6) Uani 1 1 d . . .
H6A H 0.5186 0.1164 0.9434 0.035 Uiso 1 1 calc R . .
H6B H 0.4482 0.1277 0.9530 0.035 Uiso 1 1 calc R . .
H6C H 0.4940 0.1669 0.8977 0.035 Uiso 1 1 calc R . .
C7 C 0.59975(14) -0.01052(10) 1.0045(3) 0.0223(6) Uani 1 1 d . . .
H7A H 0.6356 0.0039 1.0458 0.033 Uiso 1 1 calc R . .
H7B H 0.5920 -0.0408 1.0494 0.033 Uiso 1 1 calc R . .
H7C H 0.5650 0.0102 1.0181 0.033 Uiso 1 1 calc R . .
C8 C 0.65218(12) -0.05545(10) 0.8300(3) 0.0207(6) Uani 1 1 d . . .
H8A H 0.6550 -0.0609 0.7294 0.031 Uiso 1 1 calc R . .
H8B H 0.6384 -0.0842 0.8763 0.031 Uiso 1 1 calc R . .
H8C H 0.6918 -0.0467 0.8664 0.031 Uiso 1 1 calc R . .
H1 H 0.4323(16) 0.0355(12) 0.406(5) 0.025 Uiso 1 1 d . . .
H2 H 0.5466(15) 0.0559(12) 0.874(4) 0.025 Uiso 1 1 d . . .

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
N1 0.0209(11) 0.0163(10) 0.0080(10) 0.0011(8) -0.0020(9) -0.0006(8)
N2 0.0171(10) 0.0160(10) 0.0082(10) -0.0028(9) -0.0004(9) -0.0005(8)
N3 0.0203(11) 0.0190(11) 0.0151(12) 0.0028(9) -0.0011(10) -0.0024(9)
N4 0.0220(11) 0.0144(10) 0.0120(11) 0.0000(9) 0.0015(9) -0.0037(9)
N5 0.0194(11) 0.0138(10) 0.0162(12) -0.0007(9) -0.0018(9) -0.0006(8)
N6 0.0155(10) 0.0165(11) 0.0124(11) -0.0016(9) -0.0002(9) 0.0025(9)
B1 0.0174(14) 0.0104(12) 0.0112(13) 0.0005(10) -0.0002(11) 0.0010(10)
B2 0.0171(13) 0.0126(12) 0.0106(13) 0.0011(10) -0.0021(11) 0.0027(10)
B3 0.0122(12) 0.0118(12) 0.0121(13) -0.0001(10) 0.0007(11) -0.0038(10)
B4 0.0105(12) 0.0148(12) 0.0133(14) -0.0016(11) -0.0004(11) -0.0031(10)
C1 0.0207(13) 0.0293(15) 0.0237(15) 0.0046(12) -0.0047(12) -0.0103(12)
C2 0.0245(15) 0.0306(15) 0.0194(15) 0.0047(12) -0.0060(13) -0.0083(12)
C3 0.0354(16) 0.0255(15) 0.0146(14) 0.0020(12) 0.0039(13) -0.0056(12)
C4 0.0265(14) 0.0210(13) 0.0206(14) 0.0005(11) 0.0033(12) -0.0079(11)
C5 0.0263(14) 0.0138(11) 0.0250(15) 0.0021(11) -0.0026(12) 0.0035(10)
C6 0.0251(14) 0.0219(13) 0.0226(15) -0.0077(12) -0.0034(12) 0.0048(11)
C7 0.0313(15) 0.0210(14) 0.0145(14) 0.0004(11) -0.0019(12) 0.0050(11)
C8 0.0188(13) 0.0204(13) 0.0229(14) -0.0011(11) -0.0040(12) 0.0055(11)

_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
N1 B1 1.436(4) . ?
N1 B2 1.440(4) . ?
N1 H1 0.83(4) . ?
N2 B3 1.440(4) . ?
N2 B4 1.451(4) . ?
N2 H2 0.89(4) . ?
N3 B1 1.423(4) . ?
N3 C1 1.444(4) . ?
N3 C2 1.455(4) . ?
N4 B2 1.424(4) . ?
N4 C3 1.446(4) . ?
N4 C4 1.453(3) . ?
N5 B3 1.424(3) . ?
N5 C6 1.440(4) . ?
N5 C5 1.448(3) . ?
N6 B4 1.420(4) . ?
N6 C7 1.449(4) . ?
N6 C8 1.456(3) . ?
B1 B4 1.739(4) 2_655 ?
B2 B3 1.718(4) . ?
B4 B1 1.739(4) 2_655 ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
B1 N1 B2 130.0(2) . . ?
B1 N1 H1 116(2) . . ?
B2 N1 H1 114(2) . . ?
B3 N2 B4 130.0(2) . . ?
B3 N2 H2 115(2) . . ?
B4 N2 H2 114(2) . . ?
B1 N3 C1 123.3(2) . . ?
B1 N3 C2 124.8(2) . . ?
C1 N3 C2 111.9(2) . . ?
B2 N4 C3 124.9(2) . . ?
B2 N4 C4 122.8(2) . . ?
C3 N4 C4 112.3(2) . . ?
B3 N5 C6 125.8(2) . . ?
B3 N5 C5 123.0(2) . . ?
C6 N5 C5 111.2(2) . . ?
B4 N6 C7 126.0(2) . . ?
B4 N6 C8 122.0(2) . . ?
C7 N6 C8 112.0(2) . . ?
N3 B1 N1 118.8(3) . . ?
N3 B1 B4 117.6(2) . 2_655 ?
N1 B1 B4 123.6(2) . 2_655 ?
N4 B2 N1 119.6(2) . . ?
N4 B2 B3 119.3(2) . . ?
N1 B2 B3 120.7(2) . . ?
N5 B3 N2 119.4(2) . . ?
N5 B3 B2 117.8(2) . . ?
N2 B3 B2 122.8(2) . . ?
N6 B4 N2 117.9(2) . . ?
N6 B4 B1 119.5(2) . 2_655 ?
N2 B4 B1 122.4(2) . 2_655 ?
N3 C1 H1A 109.5 . . ?
N3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N3 C2 H2A 109.5 . . ?
N3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N4 C3 H3A 109.5 . . ?
N4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N4 C4 H4A 109.5 . . ?
N4 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N4 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N5 C5 H5A 109.5 . . ?
N5 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N5 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N5 C6 H6A 109.5 . . ?
N5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N6 C7 H7A 109.5 . . ?
N6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N6 C8 H8A 109.5 . . ?
N6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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
C1 N3 B1 N1 -178.1(3) . . . . ?
C2 N3 B1 N1 -1.0(4) . . . . ?
C1 N3 B1 B4 1.0(4) . . . 2_655 ?
C2 N3 B1 B4 178.1(3) . . . 2_655 ?
B2 N1 B1 N3 168.4(2) . . . . ?
B2 N1 B1 B4 -10.6(4) . . . 2_655 ?
C3 N4 B2 N1 -7.4(4) . . . . ?
C4 N4 B2 N1 173.9(2) . . . . ?
C3 N4 B2 B3 178.8(3) . . . . ?
C4 N4 B2 B3 0.1(4) . . . . ?
B1 N1 B2 N4 172.5(3) . . . . ?
B1 N1 B2 B3 -13.8(4) . . . . ?
C6 N5 B3 N2 1.8(4) . . . . ?
C5 N5 B3 N2 -179.6(2) . . . . ?
C6 N5 B3 B2 -178.3(2) . . . . ?
C5 N5 B3 B2 0.3(3) . . . . ?
B4 N2 B3 N5 -176.7(2) . . . . ?
B4 N2 B3 B2 3.4(4) . . . . ?
N4 B2 B3 N5 87.1(3) . . . . ?
N1 B2 B3 N5 -86.7(3) . . . . ?
N4 B2 B3 N2 -93.0(3) . . . . ?
N1 B2 B3 N2 93.3(3) . . . . ?
C7 N6 B4 N2 7.0(4) . . . . ?
C8 N6 B4 N2 -173.1(2) . . . . ?
C7 N6 B4 B1 -178.6(2) . . . 2_655 ?
C8 N6 B4 B1 1.4(3) . . . 2_655 ?
B3 N2 B4 N6 -169.7(2) . . . . ?
B3 N2 B4 B1 16.1(4) . . . 2_655 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.054