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

#######################################################################
#
#                 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_a
_audit_creation_method           SHELXL-97
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H28 B Cu N6'
_chemical_formula_weight         510.90
_chemical_melting_point          ?
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'
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y, -z'
3 'x+1/2, y+1/2, z+1/2'
4 '-x+1, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, -y, z'
7 '-x+1/2, -y+1/2, -z+1/2'
8 'x, -y+1/2, z+1/2'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   I2/a
_cell_length_a                   20.7069(6)
_cell_length_b                   9.4597(3)
_cell_length_c                   28.7537(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.040(3)
_cell_angle_gamma                90.00
_cell_volume                     5464.0(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5783
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.8615
_cell_measurement_theta_min      3.1655
_exptl_absorpt_coefficient_mu    1.317
_exptl_absorpt_correction_T_max  0.6861
_exptl_absorpt_correction_T_min  0.6194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
# SQUEEZE RESULTS (APPEND TO CIF)
loop_
  _platon_squeeze_void_nr
  _platon_squeeze_void_average_x
  _platon_squeeze_void_average_y
  _platon_squeeze_void_average_z
  _platon_squeeze_void_volume
  _platon_squeeze_void_count_electrons
         1     0.250     0.066     0.000     162.2      43.7
         2     0.750    -0.066     0.000     162.0      43.8
         3     0.250     0.434     0.500     162.0      43.8
         4     0.750     0.566     0.500     162.2      43.7
_platon_squeeze_details
;
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            11148
_diffrn_reflns_theta_full        74.29
_diffrn_reflns_theta_max         74.29
_diffrn_reflns_theta_min         3.17
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean none
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_reflns_number_gt                4446
_reflns_number_total             5422
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.639
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         5422
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0555P)²+2.7671P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1087
_refine_special_details          
;
 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. 
;
_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
Cu1 Cu 0.589341(14) 0.98509(3) 0.398496(10) 0.02031(10) Uani 1 1 d . . .
N4 N 0.67888(8) 0.9802(2) 0.39133(6) 0.0213(4) Uani 1 1 d . . .
N2 N 0.78239(8) 1.0596(2) 0.39525(6) 0.0204(4) Uani 1 1 d . . .
N12 N 0.39665(8) 0.86490(19) 0.38379(6) 0.0193(4) Uani 1 1 d . . .
C27 C 0.57367(12) 1.5255(3) 0.48406(9) 0.0319(5) Uani 1 1 d . . .
C3 C 0.72399(10) 1.0788(2) 0.40750(7) 0.0224(4) Uani 1 1 d . . .
H3 H 0.7162 1.1551 0.4258 0.027 Uiso 1 1 calc R . .
N21 N 0.63437(8) 1.17673(19) 0.53815(6) 0.0211(4) Uani 1 1 d . . .
N14 N 0.49687(8) 0.9384(2) 0.37591(6) 0.0209(4) Uani 1 1 d . . .
C13 C 0.45520(10) 0.9282(2) 0.40428(7) 0.0204(4) Uani 1 1 d . . .
H13 H 0.4654 0.9616 0.4356 0.024 Uiso 1 1 calc R . .
N23 N 0.59644(9) 1.0973(2) 0.46237(6) 0.0236(4) Uani 1 1 d . . .
C20 C 0.40096(9) 0.8307(2) 0.33753(7) 0.0180(4) Uani 1 1 d . . .
C26 C 0.54767(13) 1.4742(3) 0.43677(9) 0.0336(5) Uani 1 1 d . . .
C29 C 0.60656(11) 1.2920(2) 0.51035(8) 0.0246(4) Uani 1 1 d . . .
C5 C 0.70985(10) 0.8871(2) 0.36640(7) 0.0212(4) Uani 1 1 d . . .
C8 C 0.79376(13) 0.7334(3) 0.32379(11) 0.0389(6) Uani 1 1 d . . .
C22 C 0.62684(10) 1.0673(2) 0.50713(7) 0.0219(4) Uani 1 1 d . . .
H22 H 0.6421 0.9769 0.5167 0.026 Uiso 1 1 calc R . .
C16 C 0.48220(10) 0.8562(2) 0.29017(7) 0.0224(4) Uani 1 1 d . . .
H16 H 0.5234 0.8877 0.2869 0.027 Uiso 1 1 calc R . .
C10 C 0.77459(10) 0.9347(2) 0.36911(7) 0.0218(4) Uani 1 1 d . . .
C15 C 0.46299(9) 0.8773(2) 0.33275(7) 0.0190(4) Uani 1 1 d . . .
C19 C 0.35696(10) 0.7599(2) 0.30022(7) 0.0202(4) Uani 1 1 d . . .
H19 H 0.3158 0.7288 0.3037 0.024 Uiso 1 1 calc R . .
C17 C 0.43879(10) 0.7873(2) 0.25273(7) 0.0229(4) Uani 1 1 d . . .
C18 C 0.37630(10) 0.7374(2) 0.25810(7) 0.0225(4) Uani 1 1 d . . .
C28 C 0.60193(12) 1.4346(3) 0.52117(8) 0.0289(5) Uani 1 1 d . . .
H28 H 0.6173 1.4677 0.5524 0.035 Uiso 1 1 calc R . .
C32 C 0.33052(12) 0.6592(3) 0.21732(8) 0.0293(5) Uani 1 1 d . . .
H32A H 0.3531 0.5779 0.2090 0.044 Uiso 1 1 calc R . .
H32B H 0.3179 0.7205 0.1900 0.044 Uiso 1 1 calc R . .
H32C H 0.2914 0.6293 0.2270 0.044 Uiso 1 1 calc R . .
C24 C 0.58280(11) 1.2409(3) 0.46359(8) 0.0255(5) Uani 1 1 d . . .
C9 C 0.81702(11) 0.8560(3) 0.34769(9) 0.0302(5) Uani 1 1 d . . .
H9 H 0.8603 0.8864 0.3496 0.036 Uiso 1 1 calc R . .
C25 C 0.55205(12) 1.3319(3) 0.42662(8) 0.0315(5) Uani 1 1 d . . .
H25 H 0.5348 1.2976 0.3958 0.038 Uiso 1 1 calc R . .
C33 C 0.45769(12) 0.7678(3) 0.20547(8) 0.0338(5) Uani 1 1 d . . .
H33A H 0.4256 0.8143 0.1805 0.051 Uiso 1 1 calc R . .
H33B H 0.4586 0.6687 0.1983 0.051 Uiso 1 1 calc R . .
H33C H 0.5009 0.8079 0.2076 0.051 Uiso 1 1 calc R . .
C6 C 0.68557(11) 0.7645(3) 0.34142(8) 0.0287(5) Uani 1 1 d . . .
H6 H 0.6421 0.7350 0.3392 0.034 Uiso 1 1 calc R . .
B11 B 0.33881(11) 0.8264(3) 0.40725(8) 0.0208(5) Uani 1 1 d . . .
H11 H 0.3207 0.7335 0.3959 0.025 Uiso 1 1 calc R . .
C30 C 0.57019(14) 1.6818(3) 0.49456(10) 0.0387(6) Uani 1 1 d . . .
H30A H 0.5917 1.7345 0.4741 0.058 Uiso 1 1 calc R . .
H30B H 0.5922 1.6996 0.5275 0.058 Uiso 1 1 calc R . .
H30C H 0.5245 1.7104 0.4888 0.058 Uiso 1 1 calc R . .
C7 C 0.72716(13) 0.6870(3) 0.31985(10) 0.0369(6) Uani 1 1 d . . .
C31 C 0.51544(15) 1.5752(3) 0.39699(9) 0.0432(7) Uani 1 1 d . . .
H31A H 0.4772 1.6182 0.4045 0.065 Uiso 1 1 calc R . .
H31B H 0.5019 1.5241 0.3674 0.065 Uiso 1 1 calc R . .
H31C H 0.5468 1.6472 0.3939 0.065 Uiso 1 1 calc R . .
C34 C 0.83916(16) 0.6468(3) 0.30075(14) 0.0608(10) Uani 1 1 d . . .
H34A H 0.8804 0.6961 0.3036 0.091 Uiso 1 1 calc R . .
H34B H 0.8181 0.6323 0.2675 0.091 Uiso 1 1 calc R . .
H34C H 0.8477 0.5569 0.3166 0.091 Uiso 1 1 calc R . .
C35 C 0.70272(16) 0.5532(3) 0.29314(13) 0.0543(8) Uani 1 1 d . . .
H35A H 0.7083 0.5597 0.2610 0.081 Uiso 1 1 calc R . .
H35B H 0.6565 0.5400 0.2922 0.081 Uiso 1 1 calc R . .
H35C H 0.7278 0.4744 0.3091 0.081 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
Cu1 N4 1.9150(17) . ?
Cu1 N14 1.9183(17) . ?
Cu1 N23 2.0953(18) . ?
N4 C3 1.322(3) . ?
N4 C5 1.387(3) . ?
N2 C3 1.351(3) . ?
N2 C10 1.389(3) . ?
N2 B11 1.565(3) 6_675 ?
N12 C13 1.352(3) . ?
N12 C20 1.393(2) . ?
N12 B11 1.554(3) . ?
C27 C26 1.421(4) . ?
C27 C28 1.385(3) . ?
C27 C30 1.514(4) . ?
N21 C29 1.391(3) . ?
N21 C22 1.351(3) . ?
N21 B11 1.533(3) 5_676 ?
N14 C13 1.327(3) . ?
N14 C15 1.394(2) . ?
N23 C22 1.319(3) . ?
N23 C24 1.389(3) . ?
C20 C15 1.396(3) . ?
C20 C19 1.398(3) . ?
C26 C25 1.386(4) . ?
C26 C31 1.515(3) . ?
C29 C28 1.393(3) . ?
C29 C24 1.401(3) . ?
C5 C10 1.398(3) . ?
C5 C6 1.393(3) . ?
C8 C9 1.374(4) . ?
C8 C7 1.425(3) . ?
C8 C34 1.516(3) . ?
C16 C15 1.391(3) . ?
C16 C17 1.386(3) . ?
C10 C9 1.403(3) . ?
C19 C18 1.381(3) . ?
C17 C18 1.420(3) . ?
C17 C33 1.514(3) . ?
C18 C32 1.511(3) . ?
C24 C25 1.396(3) . ?
C6 C7 1.386(3) . ?
B11 N2 1.565(3) 6_575 ?
B11 N21 1.533(3) 5_676 ?
C7 C35 1.503(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
_geom_angle_publ_flag
N4 Cu1 N14 150.58(8) . . ?
N4 Cu1 N23 104.04(7) . . ?
N14 Cu1 N23 105.38(7) . . ?
C3 N4 Cu1 124.41(14) . . ?
C3 N4 C5 104.70(17) . . ?
C5 N4 Cu1 130.70(14) . . ?
C3 N2 C10 105.16(17) . . ?
C3 N2 B11 121.14(18) . 6_675 ?
C10 N2 B11 133.47(17) . 6_675 ?
C13 N12 C20 105.11(16) . . ?
C13 N12 B11 128.21(17) . . ?
C20 N12 B11 126.50(17) . . ?
C26 C27 C30 119.9(2) . . ?
C28 C27 C26 121.1(2) . . ?
C28 C27 C30 119.0(2) . . ?
N4 C3 N2 114.46(19) . . ?
C29 N21 B11 126.88(18) . 5_676 ?
C22 N21 C29 104.81(17) . . ?
C22 N21 B11 128.06(19) . 5_676 ?
C13 N14 Cu1 123.60(14) . . ?
C13 N14 C15 104.77(16) . . ?
C15 N14 Cu1 129.94(14) . . ?
N14 C13 N12 114.37(18) . . ?
C22 N23 Cu1 131.44(16) . . ?
C22 N23 C24 103.73(18) . . ?
C24 N23 Cu1 123.07(14) . . ?
N12 C20 C15 107.09(17) . . ?
N12 C20 C19 131.56(18) . . ?
C15 C20 C19 121.32(18) . . ?
C27 C26 C31 120.2(2) . . ?
C25 C26 C27 120.3(2) . . ?
C25 C26 C31 119.5(2) . . ?
N21 C29 C28 132.2(2) . . ?
N21 C29 C24 106.3(2) . . ?
C28 C29 C24 121.4(2) . . ?
N4 C5 C10 108.93(19) . . ?
N4 C5 C6 129.87(19) . . ?
C6 C5 C10 121.2(2) . . ?
C9 C8 C7 121.0(2) . . ?
C9 C8 C34 119.7(2) . . ?
C7 C8 C34 119.3(2) . . ?
N23 C22 N21 115.5(2) . . ?
C17 C16 C15 118.76(19) . . ?
N2 C10 C5 106.74(18) . . ?
N2 C10 C9 133.3(2) . . ?
C5 C10 C9 119.9(2) . . ?
N14 C15 C20 108.65(17) . . ?
C16 C15 N14 130.83(19) . . ?
C16 C15 C20 120.51(19) . . ?
C18 C19 C20 118.22(19) . . ?
C16 C17 C18 120.53(19) . . ?
C16 C17 C33 119.6(2) . . ?
C18 C17 C33 119.8(2) . . ?
C19 C18 C17 120.65(19) . . ?
C19 C18 C32 119.7(2) . . ?
C17 C18 C32 119.67(19) . . ?
C27 C28 C29 117.9(2) . . ?
N23 C24 C29 109.59(19) . . ?
N23 C24 C25 129.9(2) . . ?
C25 C24 C29 120.5(2) . . ?
C8 C9 C10 119.1(2) . . ?
C26 C25 C24 118.7(2) . . ?
C7 C6 C5 119.0(2) . . ?
N12 B11 N2 110.83(17) . 6_575 ?
N21 B11 N2 107.74(17) 5_676 6_575 ?
N21 B11 N12 108.86(16) 5_676 . ?
C8 C7 C35 120.0(2) . . ?
C6 C7 C8 119.7(2) . . ?
C6 C7 C35 120.3(2) . . ?

_database_code_depnum_ccdc_archive 'CCDC 992514'
