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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_17541
_database_code_depnum_ccdc_archive 'CCDC 1033621'
_audit_update_record             
;
2014-11-11 deposited with the CCDC.
2014-11-25 downloaded from the CCDC.
;
_audit_creation_date             2014-11-10
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H20 B2 Cu2 N12'
_chemical_formula_sum            'C18 H20 B2 Cu2 N12'
_chemical_formula_weight         553.16
_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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   9.0107(5)
_cell_length_b                   9.2903(6)
_cell_length_c                   15.7168(5)
_cell_angle_alpha                103.806(4)
_cell_angle_beta                 91.307(4)
_cell_angle_gamma                115.131(6)
_cell_volume                     1145.13(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4385
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.7980
_cell_measurement_theta_min      2.8900
_exptl_absorpt_coefficient_mu    2.573
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7673
_diffrn_reflns_theta_full        74.38
_diffrn_reflns_theta_max         74.38
_diffrn_reflns_theta_min         2.92
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3503
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4064
_reflns_number_total             4520
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.822
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4520
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.075
_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)+(0.0493P)²+1.0194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1001
_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 0.29887(5) -0.05808(5) -0.01822(2) 0.02940(12) Uani 1 1 d . . .
Cu2 Cu 0.86898(4) 0.75945(5) 0.42793(2) 0.02887(12) Uani 1 1 d . . .
N9 N 0.5058(2) 0.6132(2) 0.22243(12) 0.0232(4) Uani 1 1 d . . .
N22 N 1.0614(2) 0.7376(3) 0.46698(13) 0.0254(4) Uani 1 1 d . . .
N25 N 1.3543(2) 0.8200(2) 0.72013(12) 0.0234(4) Uani 1 1 d . . .
N6 N 0.2675(2) -0.1737(2) 0.07520(13) 0.0259(4) Uani 1 1 d . . .
N30 N 1.5638(2) 0.8330(3) 0.61452(13) 0.0263(4) Uani 1 1 d . . .
N14 N 0.2796(2) 0.3836(3) 0.10545(13) 0.0259(4) Uani 1 1 d . . .
N19 N 1.2805(2) 0.7857(2) 0.55755(12) 0.0230(4) Uani 1 1 d . . .
N12 N 0.7326(3) 0.7239(3) 0.32119(13) 0.0277(4) Uani 1 1 d . . .
N33 N 1.7598(3) 0.8066(3) 0.53759(14) 0.0314(5) Uani 1 1 d . . .
N3 N 0.2769(2) -0.3399(3) 0.15457(13) 0.0244(4) Uani 1 1 d . . .
N27 N 1.3012(3) 0.8401(3) 0.85868(13) 0.0275(4) Uani 1 1 d . . .
N17 N 0.2792(3) 0.1527(3) 0.02073(13) 0.0268(4) Uani 1 1 d . . .
C13 C 0.5684(3) 0.6464(3) 0.30718(15) 0.0262(5) Uani 1 1 d . . .
H13 H 0.5035 0.6182 0.3512 0.031 Uiso 1 1 calc R . .
C26 C 1.3668(3) 0.9214(3) 0.79977(15) 0.0261(5) Uani 1 1 d . . .
H26 H 1.4160 1.0361 0.8122 0.031 Uiso 1 1 calc R . .
C23 C 1.1642(3) 0.8339(3) 0.54053(15) 0.0251(5) Uani 1 1 d . . .
H23 H 1.1570 0.9253 0.5766 0.030 Uiso 1 1 calc R . .
C21 C 1.1147(3) 0.6185(3) 0.43411(16) 0.0277(5) Uani 1 1 d . . .
H21 H 1.0671 0.5330 0.3822 0.033 Uiso 1 1 calc R . .
C34 C 1.6353(3) 0.8473(3) 0.54070(17) 0.0315(5) Uani 1 1 d . . .
H34 H 1.6009 0.8820 0.4965 0.038 Uiso 1 1 calc R . .
C16 C 0.1465(3) 0.1715(3) -0.01165(16) 0.0281(5) Uani 1 1 d . . .
H16 H 0.0697 0.0995 -0.0611 0.034 Uiso 1 1 calc R . .
C7 C 0.3060(3) -0.2954(3) 0.07846(15) 0.0257(5) Uani 1 1 d . . .
H7 H 0.3483 -0.3448 0.0333 0.031 Uiso 1 1 calc R . .
C15 C 0.1452(3) 0.3111(3) 0.03979(17) 0.0290(5) Uani 1 1 d . . .
H15 H 0.0679 0.3503 0.0321 0.035 Uiso 1 1 calc R . .
C18 C 0.3553(3) 0.2826(3) 0.09030(15) 0.0260(5) Uani 1 1 d . . .
H18 H 0.4506 0.3026 0.1251 0.031 Uiso 1 1 calc R . .
C29 C 1.2743(3) 0.6623(3) 0.72885(16) 0.0265(5) Uani 1 1 d . . .
H29 H 1.2473 0.5647 0.6848 0.032 Uiso 1 1 calc R . .
C10 C 0.6399(3) 0.6749(3) 0.17871(16) 0.0284(5) Uani 1 1 d . . .
H10 H 0.6366 0.6709 0.1190 0.034 Uiso 1 1 calc R . .
C5 C 0.2105(3) -0.1379(3) 0.15451(16) 0.0274(5) Uani 1 1 d . . .
H5 H 0.1739 -0.0570 0.1719 0.033 Uiso 1 1 calc R . .
C20 C 1.2472(3) 0.6461(3) 0.48939(16) 0.0278(5) Uani 1 1 d . . .
H20 H 1.3053 0.5827 0.4827 0.033 Uiso 1 1 calc R . .
C31 C 1.6492(3) 0.7778(3) 0.66186(16) 0.0300(5) Uani 1 1 d . . .
H31 H 1.6285 0.7547 0.7160 0.036 Uiso 1 1 calc R . .
C4 C 0.2159(3) -0.2387(3) 0.20331(16) 0.0275(5) Uani 1 1 d . . .
H4 H 0.1842 -0.2391 0.2592 0.033 Uiso 1 1 calc R . .
C32 C 1.7691(3) 0.7632(3) 0.61483(17) 0.0307(5) Uani 1 1 d . . .
H32 H 1.8456 0.7292 0.6320 0.037 Uiso 1 1 calc R . .
C28 C 1.2417(3) 0.6751(3) 0.81435(16) 0.0280(5) Uani 1 1 d . . .
H28 H 1.1882 0.5872 0.8384 0.034 Uiso 1 1 calc R . .
C11 C 0.7773(3) 0.7426(3) 0.23919(17) 0.0302(5) Uani 1 1 d . . .
H11 H 0.8854 0.7938 0.2275 0.036 Uiso 1 1 calc R . .
B24 B 1.4186(3) 0.8770(3) 0.63831(17) 0.0241(5) Uani 1 1 d . . .
H24 H 1.4568 0.9966 0.6507 0.029 Uiso 1 1 calc R . .
B8 B 0.3189(3) 0.5343(4) 0.18643(18) 0.0256(5) Uani 1 1 d . . .
H8 H 0.2523 0.4986 0.2325 0.031 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 N6 1.976(2) . ?
Cu1 N27 1.945(2) 1_444 ?
Cu1 N17 1.992(2) . ?
Cu2 N22 1.9323(19) . ?
Cu2 N12 1.931(2) . ?
Cu2 N33 2.053(2) 1_455 ?
N9 C13 1.345(3) . ?
N9 C10 1.378(3) . ?
N9 B8 1.550(3) . ?
N22 C23 1.322(3) . ?
N22 C21 1.383(3) . ?
N25 C26 1.345(3) . ?
N25 C29 1.375(3) . ?
N25 B24 1.538(3) . ?
N6 C7 1.327(3) . ?
N6 C5 1.380(3) . ?
N30 C34 1.347(3) . ?
N30 C31 1.379(3) . ?
N30 B24 1.556(3) . ?
N14 C15 1.380(3) . ?
N14 C18 1.359(3) . ?
N14 B8 1.553(3) . ?
N19 C23 1.346(3) . ?
N19 C20 1.383(3) . ?
N19 B24 1.548(3) . ?
N12 C13 1.327(3) . ?
N12 C11 1.387(3) . ?
N33 Cu2 2.053(2) 1_655 ?
N33 C34 1.325(3) . ?
N33 C32 1.379(3) . ?
N3 C7 1.352(3) . ?
N3 C4 1.374(3) . ?
N3 B8 1.551(3) 1_545 ?
N27 Cu1 1.945(2) 1_666 ?
N27 C26 1.326(3) . ?
N27 C28 1.377(3) . ?
N17 C16 1.382(3) . ?
N17 C18 1.325(3) . ?
C21 C20 1.354(3) . ?
C16 C15 1.360(4) . ?
C29 C28 1.370(4) . ?
C10 C11 1.354(4) . ?
C5 C4 1.359(3) . ?
C31 C32 1.358(4) . ?
B8 N3 1.551(3) 1_565 ?

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
N6 Cu1 N17 112.71(8) . . ?
N27 Cu1 N6 123.34(9) 1_444 . ?
N27 Cu1 N17 122.73(8) 1_444 . ?
N22 Cu2 N33 107.31(8) . 1_455 ?
N12 Cu2 N22 141.13(9) . . ?
N12 Cu2 N33 110.89(8) . 1_455 ?
C13 N9 C10 106.0(2) . . ?
C13 N9 B8 125.1(2) . . ?
C10 N9 B8 128.63(19) . . ?
C23 N22 Cu2 123.81(16) . . ?
C23 N22 C21 105.08(19) . . ?
C21 N22 Cu2 130.83(17) . . ?
C26 N25 C29 105.9(2) . . ?
C26 N25 B24 124.9(2) . . ?
C29 N25 B24 129.2(2) . . ?
C7 N6 Cu1 127.95(17) . . ?
C7 N6 C5 104.6(2) . . ?
C5 N6 Cu1 127.28(16) . . ?
C34 N30 C31 105.4(2) . . ?
C34 N30 B24 125.0(2) . . ?
C31 N30 B24 129.6(2) . . ?
C15 N14 B8 126.4(2) . . ?
C18 N14 C15 105.3(2) . . ?
C18 N14 B8 127.77(19) . . ?
C23 N19 C20 105.47(19) . . ?
C23 N19 B24 124.0(2) . . ?
C20 N19 B24 130.50(19) . . ?
C13 N12 Cu2 125.12(17) . . ?
C13 N12 C11 104.4(2) . . ?
C11 N12 Cu2 129.47(17) . . ?
C34 N33 Cu2 126.15(17) . 1_655 ?
C34 N33 C32 104.8(2) . . ?
C32 N33 Cu2 127.18(17) . 1_655 ?
C7 N3 C4 105.8(2) . . ?
C7 N3 B8 128.1(2) . 1_545 ?
C4 N3 B8 125.8(2) . 1_545 ?
C26 N27 Cu1 125.18(17) . 1_666 ?
C26 N27 C28 105.5(2) . . ?
C28 N27 Cu1 129.29(17) . 1_666 ?
C16 N17 Cu1 122.42(17) . . ?
C18 N17 Cu1 131.22(16) . . ?
C18 N17 C16 104.7(2) . . ?
N12 C13 N9 112.8(2) . . ?
N27 C26 N25 112.6(2) . . ?
N22 C23 N19 112.8(2) . . ?
C20 C21 N22 109.2(2) . . ?
N33 C34 N30 113.0(2) . . ?
C15 C16 N17 109.7(2) . . ?
N6 C7 N3 112.7(2) . . ?
C16 C15 N14 107.3(2) . . ?
N17 C18 N14 112.9(2) . . ?
C28 C29 N25 107.4(2) . . ?
C11 C10 N9 107.0(2) . . ?
C4 C5 N6 109.7(2) . . ?
C21 C20 N19 107.4(2) . . ?
C32 C31 N30 107.4(2) . . ?
C5 C4 N3 107.1(2) . . ?
C31 C32 N33 109.4(2) . . ?
C29 C28 N27 108.6(2) . . ?
C10 C11 N12 109.7(2) . . ?
N25 B24 N30 109.37(19) . . ?
N25 B24 N19 110.5(2) . . ?
N19 B24 N30 107.49(18) . . ?
N9 B8 N14 108.54(19) . . ?
N9 B8 N3 110.1(2) . 1_565 ?
N3 B8 N14 107.92(19) 1_565 . ?

