# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


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#                 Cambridge Crystallographic Data Centre
#                                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_1
_database_code_depnum_ccdc_archive 'CCDC 895048'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H28 B2 Cu F8 N4'
_chemical_formula_weight         633.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu -1.9646 0.5888 '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'
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2

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

_cell_length_a                   17.5697(3)
_cell_length_b                   12.2799(2)
_cell_length_c                   9.0323(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.8490(10)
_cell_angle_gamma                90.00
_cell_volume                     1782.36(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             646
_exptl_absorpt_coefficient_mu    1.412
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6767
_exptl_absorpt_correction_T_max  0.8717
_exptl_absorpt_process_details   
;
Higashi, T. (1999). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan.
;
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Rigaku
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 10.00
_diffrn_reflns_number            15222
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.53
_diffrn_reflns_theta_max         68.19
_reflns_number_total             3252
_reflns_number_gt                2947
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0764P)^2^+1.5887P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.46(5)
_refine_ls_number_reflns         3252
_refine_ls_number_parameters     187
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1461
_refine_ls_wR_factor_gt          0.1416
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.154
_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
Cu1 Cu 0.5000 0.99950(6) 0.5000 0.0275(2) Uani 1 2 d S . .
F1 F 0.40183(11) 1.0019(3) 0.6348(2) 0.0369(4) Uani 1 1 d D . .
F3 F 0.3421(3) 1.1222(3) 0.7331(6) 0.0994(13) Uani 1 1 d D . .
F4 F 0.2745(2) 0.9758(6) 0.6297(5) 0.142(2) Uani 1 1 d D . .
F2 F 0.3892(3) 0.9783(6) 0.8692(4) 0.136(2) Uani 1 1 d D . .
N1 N 0.4330(3) 1.1172(3) 0.3477(5) 0.0280(10) Uani 1 1 d . . .
N2 N 0.5680(3) 0.8809(3) 0.6564(5) 0.0311(11) Uani 1 1 d . . .
C5 C 0.3808(4) 1.1768(3) 0.3852(7) 0.0368(14) Uani 1 1 d . . .
H5 H 0.3720 1.1577 0.4790 0.044 Uiso 1 1 calc R . .
C4 C 0.3381(4) 1.2657(4) 0.2951(8) 0.0465(15) Uani 1 1 d . . .
H4 H 0.3024 1.3061 0.3303 0.056 Uiso 1 1 calc R . .
C3 C 0.3465(3) 1.2973(4) 0.1531(7) 0.0305(12) Uani 1 1 d . . .
C2 C 0.3987(4) 1.2302(4) 0.1138(6) 0.0367(12) Uani 1 1 d . . .
H2 H 0.4052 1.2425 0.0157 0.044 Uiso 1 1 calc R . .
C1 C 0.4410(4) 1.1471(4) 0.2118(7) 0.0409(15) Uani 1 1 d . . .
H1 H 0.4790 1.1073 0.1820 0.049 Uiso 1 1 calc R . .
C13 C 0.5555(3) 0.8548(5) 0.7865(7) 0.0396(14) Uani 1 1 d . . .
H13 H 0.5205 0.8988 0.8189 0.048 Uiso 1 1 calc R . .
C12 C 0.5944(4) 0.7605(4) 0.8790(8) 0.0494(16) Uani 1 1 d . . .
H12 H 0.5810 0.7377 0.9661 0.059 Uiso 1 1 calc R . .
C11 C 0.6510(3) 0.7034(3) 0.8413(6) 0.0290(11) Uani 1 1 d . . .
C10 C 0.6673(4) 0.7363(4) 0.7132(7) 0.0405(13) Uani 1 1 d . . .
H10 H 0.7084 0.7001 0.6882 0.049 Uiso 1 1 calc R . .
C9 C 0.6243(4) 0.8214(5) 0.6214(8) 0.0497(18) Uani 1 1 d . . .
H9 H 0.6338 0.8405 0.5284 0.060 Uiso 1 1 calc R . .
C6 C 0.3044(3) 1.3955(4) 0.0581(7) 0.0336(12) Uani 1 1 d . . .
H6A H 0.2457 1.3978 0.0452 0.040 Uiso 1 1 calc R . .
H6B H 0.3051 1.3927 -0.0509 0.040 Uiso 1 1 calc R . .
C7 C 0.35073(18) 1.4968(4) 0.1488(4) 0.0306(6) Uani 1 1 d . . .
H7A H 0.4080 1.4964 0.1535 0.037 Uiso 1 1 calc R . .
H7B H 0.3546 1.4948 0.2612 0.037 Uiso 1 1 calc R . .
C8 C 0.3066(3) 1.6019(4) 0.0664(6) 0.0337(12) Uani 1 1 d . . .
H8A H 0.3053 1.6053 -0.0442 0.040 Uiso 1 1 calc R . .
H8B H 0.2484 1.6002 0.0564 0.040 Uiso 1 1 calc R . .
B1 B 0.3511(2) 1.0139(4) 0.7181(4) 0.0410(11) Uani 1 1 d 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
Cu1 0.0317(3) 0.0165(3) 0.0362(4) 0.000 0.0157(3) 0.000
F1 0.0436(10) 0.0284(9) 0.0492(10) -0.0057(18) 0.0296(8) -0.0007(17)
F3 0.127(3) 0.073(2) 0.139(3) -0.013(2) 0.096(3) 0.032(2)
F4 0.0490(18) 0.257(7) 0.121(3) 0.002(4) 0.0357(19) -0.059(3)
F2 0.126(3) 0.236(7) 0.064(2) 0.081(4) 0.056(2) 0.075(4)
N1 0.033(2) 0.023(2) 0.032(2) -0.0170(17) 0.018(2) -0.0155(17)
N2 0.031(2) 0.014(2) 0.048(3) 0.0074(19) 0.016(2) 0.0092(17)
C5 0.056(4) 0.022(2) 0.049(4) 0.013(2) 0.038(3) 0.004(2)
C4 0.061(4) 0.033(3) 0.060(4) -0.005(3) 0.040(3) 0.013(3)
C3 0.026(3) 0.026(3) 0.040(3) -0.009(2) 0.013(2) -0.007(2)
C2 0.050(3) 0.032(2) 0.030(2) -0.006(2) 0.019(2) 0.007(2)
C1 0.063(4) 0.019(2) 0.048(4) 0.009(2) 0.030(3) 0.019(3)
C13 0.036(3) 0.048(3) 0.046(4) 0.004(3) 0.028(3) 0.009(3)
C12 0.059(4) 0.037(3) 0.069(4) 0.029(3) 0.044(3) 0.014(3)
C11 0.033(3) 0.014(2) 0.034(3) 0.004(2) 0.007(2) 0.000(2)
C10 0.037(3) 0.041(3) 0.048(3) 0.017(3) 0.021(3) 0.018(2)
C9 0.052(4) 0.062(4) 0.045(4) 0.012(3) 0.029(3) 0.031(3)
C6 0.035(3) 0.019(2) 0.045(3) 0.005(2) 0.015(3) 0.000(2)
C7 0.0306(14) 0.0211(13) 0.0340(15) 0.005(3) 0.0067(12) -0.001(3)
C8 0.035(3) 0.025(3) 0.031(3) 0.007(2) 0.003(2) 0.002(2)
B1 0.044(2) 0.041(3) 0.049(2) 0.001(2) 0.0292(19) 0.000(2)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 2.014(4) 2_656 ?
Cu1 N1 2.014(4) . ?
Cu1 N2 2.045(4) 2_656 ?
Cu1 N2 2.045(4) . ?
F1 B1 1.388(3) . ?
F3 B1 1.353(4) . ?
F4 B1 1.341(4) . ?
F2 B1 1.328(4) . ?
N1 C5 1.320(6) . ?
N1 C1 1.342(6) . ?
N2 C13 1.318(6) . ?
N2 C9 1.366(6) . ?
C5 C4 1.387(7) . ?
C5 H5 0.9500 . ?
C4 C3 1.404(8) . ?
C4 H4 0.9500 . ?
C3 C2 1.382(7) . ?
C3 C6 1.491(7) . ?
C2 C1 1.358(7) . ?
C2 H2 0.9500 . ?
C1 H1 0.9500 . ?
C13 C12 1.429(8) . ?
C13 H13 0.9500 . ?
C12 C11 1.369(7) . ?
C12 H12 0.9500 . ?
C11 C10 1.360(7) . ?
C11 C8 1.517(7) 2_646 ?
C10 C9 1.358(7) . ?
C10 H10 0.9500 . ?
C9 H9 0.9500 . ?
C6 C7 1.531(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.534(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C11 1.517(7) 2_666 ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?

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
N1 Cu1 N1 88.34(19) 2_656 . ?
N1 Cu1 N2 179.45(19) 2_656 2_656 ?
N1 Cu1 N2 91.27(9) . 2_656 ?
N1 Cu1 N2 91.27(9) 2_656 . ?
N1 Cu1 N2 179.45(19) . . ?
N2 Cu1 N2 89.1(2) 2_656 . ?
C5 N1 C1 115.1(4) . . ?
C5 N1 Cu1 119.8(3) . . ?
C1 N1 Cu1 124.9(3) . . ?
C13 N2 C9 118.3(4) . . ?
C13 N2 Cu1 121.9(3) . . ?
C9 N2 Cu1 119.7(4) . . ?
N1 C5 C4 123.6(5) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
C5 C4 C3 121.4(4) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C2 C3 C4 113.3(5) . . ?
C2 C3 C6 124.1(5) . . ?
C4 C3 C6 122.6(4) . . ?
C1 C2 C3 121.7(5) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
N1 C1 C2 124.7(5) . . ?
N1 C1 H1 117.7 . . ?
C2 C1 H1 117.7 . . ?
N2 C13 C12 120.4(5) . . ?
N2 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C11 C12 C13 119.5(5) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C10 C11 C12 118.9(5) . . ?
C10 C11 C8 119.1(5) . 2_646 ?
C12 C11 C8 121.9(5) . 2_646 ?
C9 C10 C11 119.5(5) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C9 N2 123.1(5) . . ?
C10 C9 H9 118.4 . . ?
N2 C9 H9 118.4 . . ?
C3 C6 C7 108.4(4) . . ?
C3 C6 H6A 110.0 . . ?
C7 C6 H6A 110.0 . . ?
C3 C6 H6B 110.0 . . ?
C7 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
C6 C7 C8 111.7(2) . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C11 C8 C7 112.7(4) 2_666 . ?
C11 C8 H8A 109.1 2_666 . ?
C7 C8 H8A 109.1 . . ?
C11 C8 H8B 109.1 2_666 . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
F2 B1 F4 117.8(4) . . ?
F2 B1 F3 104.5(5) . . ?
F4 B1 F3 105.9(5) . . ?
F2 B1 F1 110.7(3) . . ?
F4 B1 F1 110.5(3) . . ?
F3 B1 F1 106.6(3) . . ?

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
N1 Cu1 N1 C5 -70.9(3) 2_656 . . . ?
N2 Cu1 N1 C5 109.5(4) 2_656 . . . ?
N2 Cu1 N1 C5 -26(22) . . . . ?
N1 Cu1 N1 C1 103.8(4) 2_656 . . . ?
N2 Cu1 N1 C1 -75.8(4) 2_656 . . . ?
N2 Cu1 N1 C1 149(22) . . . . ?
N1 Cu1 N2 C13 77.5(4) 2_656 . . . ?
N1 Cu1 N2 C13 32(22) . . . . ?
N2 Cu1 N2 C13 -102.9(4) 2_656 . . . ?
N1 Cu1 N2 C9 -106.9(4) 2_656 . . . ?
N1 Cu1 N2 C9 -152(22) . . . . ?
N2 Cu1 N2 C9 72.7(4) 2_656 . . . ?
C1 N1 C5 C4 -1.4(7) . . . . ?
Cu1 N1 C5 C4 173.8(4) . . . . ?
N1 C5 C4 C3 1.4(9) . . . . ?
C5 C4 C3 C2 1.5(8) . . . . ?
C5 C4 C3 C6 -177.2(5) . . . . ?
C4 C3 C2 C1 -4.2(8) . . . . ?
C6 C3 C2 C1 174.4(5) . . . . ?
C5 N1 C1 C2 -1.5(8) . . . . ?
Cu1 N1 C1 C2 -176.5(4) . . . . ?
C3 C2 C1 N1 4.6(9) . . . . ?
C9 N2 C13 C12 -5.7(8) . . . . ?
Cu1 N2 C13 C12 170.0(4) . . . . ?
N2 C13 C12 C11 6.4(10) . . . . ?
C13 C12 C11 C10 -1.8(9) . . . . ?
C13 C12 C11 C8 -179.1(5) . . . 2_646 ?
C12 C11 C10 C9 -3.1(9) . . . . ?
C8 C11 C10 C9 174.3(5) 2_646 . . . ?
C11 C10 C9 N2 3.9(9) . . . . ?
C13 N2 C9 C10 0.6(9) . . . . ?
Cu1 N2 C9 C10 -175.1(5) . . . . ?
C2 C3 C6 C7 -103.3(6) . . . . ?
C4 C3 C6 C7 75.2(6) . . . . ?
C3 C6 C7 C8 -175.0(5) . . . . ?
C6 C7 C8 C11 177.1(5) . . . 2_666 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        68.19
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.065