# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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/access/V1 
# 
# Audit and citation data items may have 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_1
_database_code_depnum_ccdc_archive 'CCDC 1019508'
_audit_update_record             
;
2014-08-15 deposited with the CCDC.
2015-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H10 B10 N2 Na2 O17'
_chemical_formula_weight         488.20

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 '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/c

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

_cell_length_a                   21.9507(10)
_cell_length_b                   6.4172(2)
_cell_length_c                   11.0598(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.407(4)
_cell_angle_gamma                90.00
_cell_volume                     1515.45(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1860
_cell_measurement_theta_min      2.9774
_cell_measurement_theta_max      29.1416

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.140
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9308
_exptl_absorpt_correction_T_max  0.9418
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Gemini A Ultra diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            3220
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.31
_diffrn_reflns_theta_max         25.19
_reflns_number_total             1369
_reflns_number_gt                1180
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEXII (Bruker, 2006)'
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0329P)²+2.7902P] where P=(Fo²+2Fc²)/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         1369
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0802
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
B1 B 0.05761(11) 0.1679(4) 0.7427(2) 0.0130(5) Uani 1 1 d . . .
B2 B 0.14858(10) 0.1603(4) 0.6443(2) 0.0108(5) Uani 1 1 d . . .
B3 B 0.15431(11) 0.3632(4) 0.8457(2) 0.0117(5) Uani 1 1 d . . .
B4 B 0.18481(10) -0.0825(4) 0.5042(2) 0.0119(5) Uani 1 1 d . . .
B5 B 0.16331(11) 0.2676(4) 0.4335(2) 0.0117(5) Uani 1 1 d . . .
O1 O 0.18160(6) 0.2704(2) 0.75232(12) 0.0115(3) Uani 1 1 d . . .
O2 O 0.18295(6) -0.0291(2) 0.62243(12) 0.0122(3) Uani 1 1 d . . .
O3 O 0.14045(6) 0.3046(2) 0.53517(12) 0.0141(3) Uani 1 1 d . . .
O4 O 0.08521(7) 0.3202(2) 0.82191(13) 0.0183(4) Uani 1 1 d . . .
O5 O 0.18259(7) -0.2873(2) 0.47277(13) 0.0151(3) Uani 1 1 d . . .
O6 O 0.18648(7) 0.0708(2) 0.41635(13) 0.0180(4) Uani 1 1 d . . .
O7 O 0.16394(7) 0.4096(2) 0.34277(13) 0.0148(3) Uani 1 1 d . . .
O8 O 0.08527(6) 0.0874(2) 0.65538(13) 0.0142(3) Uani 1 1 d . . .
O9 O 0.0000 0.0898(3) 0.7500 0.0201(5) Uani 1 2 d S . .
Na1 Na 0.22959(4) 0.56639(14) 0.68629(8) 0.0206(2) Uani 1 1 d . . .
C1 C 0.00300(10) 0.5942(4) 0.5428(2) 0.0208(5) Uani 1 1 d . . .
H1A H -0.0222 0.7075 0.4995 0.025 Uiso 1 1 calc R . .
H1B H -0.0129 0.5589 0.6150 0.025 Uiso 1 1 calc R . .
N1 N 0.06864(9) 0.6632(3) 0.5836(2) 0.0268(5) Uani 1 1 d . . .
H1C H 0.0707 0.7735 0.6332 0.040 Uiso 1 1 calc R . .
H1D H 0.0832 0.6975 0.5175 0.040 Uiso 1 1 calc R . .
H1E H 0.0917 0.5603 0.6247 0.040 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
B1 O8 1.356(3) . ?
B1 O4 1.358(3) . ?
B1 O9 1.380(2) . ?
B2 O1 1.432(3) . ?
B2 O2 1.480(3) . ?
B2 O8 1.498(3) . ?
B2 O3 1.499(3) . ?
B2 Na1 2.950(2) 4_546 ?
B2 Na1 3.128(2) . ?
B3 O1 1.438(3) . ?
B3 O7 1.475(3) 6_566 ?
B3 O5 1.481(3) 6_556 ?
B3 O4 1.503(3) . ?
B3 Na1 2.982(2) . ?
B4 O5 1.358(3) . ?
B4 O2 1.361(3) . ?
B4 O6 1.389(3) . ?
B4 Na1 3.030(2) 1_545 ?
B4 Na1 3.133(2) 7_556 ?
B5 O3 1.354(3) . ?
B5 O7 1.358(3) . ?
B5 O6 1.391(3) . ?
O1 Na1 2.3154(16) 4_546 ?
O1 Na1 2.3681(16) . ?
O2 Na1 2.5794(16) 4_546 ?
O2 Na1 2.8195(16) 1_545 ?
O3 Na1 2.8156(17) . ?
O5 B3 1.481(3) 6 ?
O5 Na1 2.5284(16) 1_545 ?
O6 Na1 2.5352(17) 7_556 ?
O7 B3 1.475(3) 6_565 ?
O7 Na1 2.5005(16) 6_565 ?
O9 B1 1.380(2) 2_556 ?
Na1 O1 2.3154(16) 4_556 ?
Na1 O7 2.5005(16) 6_566 ?
Na1 O5 2.5284(16) 1_565 ?
Na1 O6 2.5352(17) 7_556 ?
Na1 O2 2.5794(16) 4_556 ?
Na1 O2 2.8195(16) 1_565 ?
Na1 B2 2.950(2) 4_556 ?
Na1 B4 3.030(2) 1_565 ?
C1 N1 1.475(3) . ?
C1 C1 1.523(4) 5_566 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
N1 H1C 0.8900 . ?
N1 H1D 0.8900 . ?
N1 H1E 0.8900 . ?

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
O8 B1 O4 121.80(19) . . ?
O8 B1 O9 118.12(19) . . ?
O4 B1 O9 120.08(18) . . ?
O1 B2 O2 111.30(17) . . ?
O1 B2 O8 112.70(16) . . ?
O2 B2 O8 105.96(16) . . ?
O1 B2 O3 108.03(17) . . ?
O2 B2 O3 110.21(16) . . ?
O8 B2 O3 108.61(16) . . ?
O1 B2 Na1 50.35(9) . 4_546 ?
O2 B2 Na1 60.96(10) . 4_546 ?
O8 B2 Na1 127.31(13) . 4_546 ?
O3 B2 Na1 123.96(13) . 4_546 ?
O1 B2 Na1 45.95(9) . . ?
O2 B2 Na1 114.49(13) . . ?
O8 B2 Na1 138.95(13) . . ?
O3 B2 Na1 64.04(10) . . ?
Na1 B2 Na1 71.06(5) 4_546 . ?
O1 B3 O7 107.93(17) . 6_566 ?
O1 B3 O5 113.12(17) . 6_556 ?
O7 B3 O5 108.39(17) 6_566 6_556 ?
O1 B3 O4 111.70(17) . . ?
O7 B3 O4 108.73(17) 6_566 . ?
O5 B3 O4 106.86(16) 6_556 . ?
O1 B3 Na1 51.39(9) . . ?
O7 B3 Na1 56.81(10) 6_566 . ?
O5 B3 Na1 122.48(13) 6_556 . ?
O4 B3 Na1 130.65(13) . . ?
O5 B4 O2 118.84(19) . . ?
O5 B4 O6 120.73(18) . . ?
O2 B4 O6 120.38(19) . . ?
O5 B4 Na1 55.75(10) . 1_545 ?
O2 B4 Na1 68.05(11) . 1_545 ?
O6 B4 Na1 159.12(15) . 1_545 ?
O5 B4 Na1 81.43(12) . 7_556 ?
O2 B4 Na1 142.55(14) . 7_556 ?
O6 B4 Na1 52.33(10) . 7_556 ?
Na1 B4 Na1 108.58(7) 1_545 7_556 ?
O3 B5 O7 124.41(19) . . ?
O3 B5 O6 119.37(19) . . ?
O7 B5 O6 116.19(18) . . ?
B2 O1 B3 126.09(16) . . ?
B2 O1 Na1 101.22(12) . 4_546 ?
B3 O1 Na1 119.09(12) . 4_546 ?
B2 O1 Na1 108.30(12) . . ?
B3 O1 Na1 100.29(12) . . ?
Na1 O1 Na1 98.02(5) 4_546 . ?
B4 O2 B2 119.59(16) . . ?
B4 O2 Na1 131.69(12) . 4_546 ?
B2 O2 Na1 88.93(11) . 4_546 ?
B4 O2 Na1 85.36(12) . 1_545 ?
B2 O2 Na1 152.18(12) . 1_545 ?
Na1 O2 Na1 81.68(4) 4_546 1_545 ?
B5 O3 B2 124.22(17) . . ?
B5 O3 Na1 104.91(12) . . ?
B2 O3 Na1 87.37(11) . . ?
B1 O4 B3 121.73(16) . . ?
B4 O5 B3 122.95(16) . 6 ?
B4 O5 Na1 97.90(12) . 1_545 ?
B3 O5 Na1 139.00(12) 6 1_545 ?
B4 O6 B5 118.50(17) . . ?
B4 O6 Na1 101.97(12) . 7_556 ?
B5 O6 Na1 134.68(13) . 7_556 ?
B5 O7 B3 128.38(17) . 6_565 ?
B5 O7 Na1 131.24(13) . 6_565 ?
B3 O7 Na1 93.60(11) 6_565 6_565 ?
B1 O8 B2 121.08(16) . . ?
B1 O9 B1 137.4(3) 2_556 . ?
O1 Na1 O1 140.14(5) 4_556 . ?
O1 Na1 O7 110.08(6) 4_556 6_566 ?
O1 Na1 O7 57.80(5) . 6_566 ?
O1 Na1 O5 101.38(6) 4_556 1_565 ?
O1 Na1 O5 118.14(6) . 1_565 ?
O7 Na1 O5 116.59(6) 6_566 1_565 ?
O1 Na1 O6 71.20(5) 4_556 7_556 ?
O1 Na1 O6 106.32(6) . 7_556 ?
O7 Na1 O6 157.92(6) 6_566 7_556 ?
O5 Na1 O6 83.81(5) 1_565 7_556 ?
O1 Na1 O2 58.53(5) 4_556 4_556 ?
O1 Na1 O2 81.73(5) . 4_556 ?
O7 Na1 O2 83.44(5) 6_566 4_556 ?
O5 Na1 O2 156.80(6) 1_565 4_556 ?
O6 Na1 O2 78.74(5) 7_556 4_556 ?
O1 Na1 O3 158.96(6) 4_556 . ?
O1 Na1 O3 53.62(4) . . ?
O7 Na1 O3 90.86(5) 6_566 . ?
O5 Na1 O3 65.82(5) 1_565 . ?
O6 Na1 O3 90.24(5) 7_556 . ?
O2 Na1 O3 128.88(5) 4_556 . ?
O1 Na1 O2 77.59(5) 4_556 1_565 ?
O1 Na1 O2 130.85(6) . 1_565 ?
O7 Na1 O2 83.25(5) 6_566 1_565 ?
O5 Na1 O2 51.56(4) 1_565 1_565 ?
O6 Na1 O2 117.83(5) 7_556 1_565 ?
O2 Na1 O2 125.60(6) 4_556 1_565 ?
O3 Na1 O2 103.81(5) . 1_565 ?
O1 Na1 B2 28.43(6) 4_556 4_556 ?
O1 Na1 B2 111.75(6) . 4_556 ?
O7 Na1 B2 97.53(6) 6_566 4_556 ?
O5 Na1 B2 129.11(6) 1_565 4_556 ?
O6 Na1 B2 73.10(6) 7_556 4_556 ?
O2 Na1 B2 30.10(5) 4_556 4_556 ?
O3 Na1 B2 154.39(6) . 4_556 ?
O2 Na1 B2 101.19(6) 1_565 4_556 ?
O1 Na1 B3 128.19(6) 4_556 . ?
O1 Na1 B3 28.32(6) . . ?
O7 Na1 B3 29.59(5) 6_566 . ?
O5 Na1 B3 123.55(6) 1_565 . ?
O6 Na1 B3 132.29(6) 7_556 . ?
O2 Na1 B3 79.64(6) 4_556 . ?
O3 Na1 B3 71.70(6) . . ?
O2 Na1 B3 109.39(6) 1_565 . ?
B2 Na1 B3 105.01(7) 4_556 . ?
O1 Na1 B4 84.01(6) 4_556 1_565 ?
O1 Na1 B4 134.63(6) . 1_565 ?
O7 Na1 B4 105.29(6) 6_566 1_565 ?
O5 Na1 B4 26.35(5) 1_565 1_565 ?
O6 Na1 B4 96.78(6) 7_556 1_565 ?
O2 Na1 B4 141.89(6) 4_556 1_565 ?
O3 Na1 B4 88.60(6) . 1_565 ?
O2 Na1 B4 26.60(5) 1_565 1_565 ?
B2 Na1 B4 112.13(7) 4_556 1_565 ?
B3 Na1 B4 125.40(7) . 1_565 ?
O1 Na1 B2 157.74(6) 4_556 . ?
O1 Na1 B2 25.75(5) . . ?
O7 Na1 B2 75.82(6) 6_566 . ?
O5 Na1 B2 94.36(6) 1_565 . ?
O6 Na1 B2 95.25(6) 7_556 . ?
O2 Na1 B2 102.30(6) 4_556 . ?
O3 Na1 B2 28.60(5) . . ?
O2 Na1 B2 124.67(6) 1_565 . ?
B2 Na1 B2 131.67(7) 4_556 . ?
B3 Na1 B2 49.42(6) . . ?
B4 Na1 B2 115.81(7) 1_565 . ?
N1 C1 C1 111.5(2) . 5_566 ?
N1 C1 H1A 109.3 . . ?
C1 C1 H1A 109.3 5_566 . ?
N1 C1 H1B 109.3 . . ?
C1 C1 H1B 109.3 5_566 . ?
H1A C1 H1B 108.0 . . ?
C1 N1 H1C 109.5 . . ?
C1 N1 H1D 109.5 . . ?
H1C N1 H1D 109.5 . . ?
C1 N1 H1E 109.5 . . ?
H1C N1 H1E 109.5 . . ?
H1D N1 H1E 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1E O3 0.89 2.30 2.908(2) 125.1 .
N1 H1C O8 0.89 2.05 2.835(2) 147.2 1_565
N1 H1D O5 0.89 2.35 3.047(3) 135.3 1_565
N1 H1D O4 0.89 2.18 3.001(3) 153.8 6_565
N1 H1E O7 0.89 2.57 3.167(3) 125.3 6_566

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.19
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.059
