# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1473011'
_audit_update_record             
;
2016-04-08 deposited with the CCDC.
2016-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H14 B10 O2'
_chemical_formula_weight         202.25

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   9.9852(4)
_cell_length_b                   10.5210(5)
_cell_length_c                   22.3329(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.840(3)
_cell_angle_gamma                90.00
_cell_volume                     2324.24(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    71
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6538
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31096
_diffrn_reflns_av_R_equivalents  0.0804
_diffrn_reflns_av_sigmaI/netI    0.0747
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         25.25
_reflns_number_total             4196
_reflns_number_gt                1868
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS SHELXTL'

_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)+(0.1928P)²+2.1729P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4196
_refine_ls_number_parameters     309
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.2063
_refine_ls_R_factor_gt           0.1094
_refine_ls_wR_factor_ref         0.3778
_refine_ls_wR_factor_gt          0.2933
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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
O1' O 1.0328(4) 0.3776(4) 0.11311(17) 0.0797(13) Uani 1 1 d . B .
C12' C 1.2331(6) 0.3664(6) 0.0713(3) 0.0804(19) Uani 1 1 d . B .
H12A H 1.2683 0.3263 0.0381 0.121 Uiso 1 1 calc R . .
H12B H 1.2770 0.3318 0.1087 0.121 Uiso 1 1 calc R . .
H12C H 1.2496 0.4562 0.0704 0.121 Uiso 1 1 calc R . .
O1 O 0.6721(4) -0.0160(4) 0.95239(19) 0.0945(15) Uani 1 1 d . A .
O2 O 0.8622(12) -0.032(5) 1.0205(9) 0.165(9) Uani 0.72(7) 1 d PD A 1
O02 O 0.840(3) 0.023(3) 1.0258(13) 0.070(12) Uani 0.28(7) 1 d PD A 2
C1 C 0.8370(5) 0.1646(5) 0.9147(2) 0.0621(15) Uani 1 1 d . A .
H1 H 0.8726 0.1931 0.9615 0.074 Uiso 1 1 calc R . .
C2 C 0.8781(5) 0.0284(5) 0.8882(2) 0.0601(15) Uani 1 1 d . A .
H2 H 0.9422 -0.0387 0.9171 0.072 Uiso 1 1 calc R . .
C11 C 0.7407(7) -0.0364(8) 1.0086(3) 0.095(2) Uani 1 1 d D . .
C12 C 0.6584(7) -0.1054(7) 1.0512(3) 0.105(2) Uani 1 1 d . A .
H12D H 0.7120 -0.1150 1.0900 0.157 Uiso 1 1 calc R . .
H12E H 0.6327 -0.1877 1.0349 0.157 Uiso 1 1 calc R . .
H12F H 0.5788 -0.0570 1.0554 0.157 Uiso 1 1 calc R . .
B3' B 0.8945(6) 0.3816(7) 0.1186(3) 0.0647(18) Uani 1 1 d . . .
B4' B 0.7839(7) 0.2567(7) 0.1240(4) 0.078(2) Uani 1 1 d . . .
H4' H 0.8141 0.1599 0.1130 0.094 Uiso 1 1 calc R . .
B5' B 0.6871(8) 0.2838(9) 0.1811(4) 0.096(3) Uani 1 1 d . . .
H5' H 0.6532 0.2051 0.2078 0.116 Uiso 1 1 calc R . .
B6' B 0.7338(7) 0.4287(9) 0.2148(3) 0.089(3) Uani 1 1 d . . .
H6' H 0.7326 0.4472 0.2632 0.107 Uiso 1 1 calc R . .
B7' B 0.7928(7) 0.5177(6) 0.1014(3) 0.0659(18) Uani 1 1 d . . .
H7' H 0.8294 0.5969 0.0759 0.079 Uiso 1 1 calc R . .
B8' B 0.7452(6) 0.3732(7) 0.0672(3) 0.071(2) Uani 1 1 d . . .
H8' H 0.7482 0.3561 0.0188 0.085 Uiso 1 1 calc R . .
B9' B 0.6173(7) 0.3084(8) 0.1069(4) 0.087(2) Uani 1 1 d . . .
H9' H 0.5371 0.2466 0.0843 0.105 Uiso 1 1 calc R . .
B10' B 0.5854(7) 0.4185(8) 0.1627(3) 0.082(2) Uani 1 1 d . . .
H10' H 0.4847 0.4306 0.1765 0.098 Uiso 1 1 calc R . .
B11' B 0.6944(7) 0.5457(8) 0.1594(3) 0.080(2) Uani 1 1 d . . .
H11' H 0.6667 0.6428 0.1713 0.096 Uiso 1 1 calc R . .
B12' B 0.6218(7) 0.4715(7) 0.0929(3) 0.077(2) Uani 1 1 d . . .
H12' H 0.5438 0.5181 0.0607 0.093 Uiso 1 1 calc R . .
B3 B 0.7184(6) 0.0473(6) 0.9044(3) 0.0587(16) Uani 1 1 d . . .
B4 B 0.6817(6) 0.2084(6) 0.8854(3) 0.0663(18) Uani 1 1 d . A .
H4 H 0.6130 0.2648 0.9094 0.080 Uiso 1 1 calc R . .
B5 B 0.8249(7) 0.2774(7) 0.8608(3) 0.0711(19) Uani 1 1 d . . .
H5 H 0.8490 0.3785 0.8689 0.085 Uiso 1 1 calc R A .
B6 B 0.9552(6) 0.1611(7) 0.8649(3) 0.0661(18) Uani 1 1 d . A .
H6 H 1.0633 0.1838 0.8761 0.079 Uiso 1 1 calc R . .
B7 B 0.7548(7) -0.0307(7) 0.8378(3) 0.0697(19) Uani 1 1 d . A .
H7 H 0.7345 -0.1327 0.8304 0.084 Uiso 1 1 calc R . .
B8 B 0.6258(7) 0.0842(7) 0.8344(3) 0.0712(19) Uani 1 1 d . A .
H8 H 0.5183 0.0584 0.8245 0.085 Uiso 1 1 calc R . .
B9 B 0.6889(7) 0.2260(7) 0.8075(3) 0.071(2) Uani 1 1 d . A .
H9 H 0.6228 0.2931 0.7796 0.085 Uiso 1 1 calc R . .
B10 B 0.8597(7) 0.2003(7) 0.7949(3) 0.0702(19) Uani 1 1 d . A .
H10 H 0.9052 0.2506 0.7594 0.084 Uiso 1 1 calc R . .
B11 B 0.8977(7) 0.0389(7) 0.8139(3) 0.0689(19) Uani 1 1 d . . .
H11 H 0.9691 -0.0168 0.7912 0.083 Uiso 1 1 calc R A .
B12 B 0.7328(7) 0.0784(7) 0.7787(3) 0.072(2) Uani 1 1 d . A .
H12 H 0.6951 0.0492 0.7321 0.086 Uiso 1 1 calc R . .
C1' C 0.8473(6) 0.3319(6) 0.1869(3) 0.0755(18) Uani 1 1 d . . .
H1' H 0.9244 0.2847 0.2193 0.091 Uiso 1 1 calc R . .
C2' C 0.8516(6) 0.4837(6) 0.1744(3) 0.0750(18) Uani 1 1 d . . .
H2' H 0.9326 0.5427 0.1984 0.090 Uiso 1 1 calc R . .
C11' C 1.0890(6) 0.3435(8) 0.0664(3) 0.083(2) Uani 1 1 d D . .
O2' O 1.0179(11) 0.355(3) 0.0169(4) 0.245(16) Uani 0.57(2) 1 d PD B 1
O2" O 1.0373(11) 0.2509(8) 0.0400(6) 0.063(5) Uani 0.43(2) 1 d PD B 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
O1' C11' 1.300(7) . ?
O1' B3' 1.404(7) . ?
C12' C11' 1.448(8) . ?
O1 C11 1.362(7) . ?
O1 B3 1.393(7) . ?
O2 C11 1.207(9) . ?
O02 C11 1.189(10) . ?
C1 C2 1.624(7) . ?
C1 B4 1.664(8) . ?
C1 B5 1.682(9) . ?
C1 B3 1.705(8) . ?
C1 B6 1.729(8) . ?
C2 B7 1.671(8) . ?
C2 B3 1.695(8) . ?
C2 B11 1.700(8) . ?
C2 B6 1.709(8) . ?
C11 C12 1.523(9) . ?
B3' B4' 1.731(10) . ?
B3' C1' 1.737(8) . ?
B3' C2' 1.742(8) . ?
B3' B8' 1.756(9) . ?
B3' B7' 1.768(9) . ?
B4' C1' 1.661(9) . ?
B4' B5' 1.726(11) . ?
B4' B9' 1.742(10) . ?
B4' B8' 1.769(10) . ?
B5' C1' 1.666(9) . ?
B5' B9' 1.728(11) . ?
B5' B6' 1.735(12) . ?
B5' B10' 1.759(12) . ?
B6' C2' 1.680(10) . ?
B6' C1' 1.703(10) . ?
B6' B11' 1.752(12) . ?
B6' B10' 1.758(10) . ?
B7' C2' 1.694(9) . ?
B7' B8' 1.739(9) . ?
B7' B11' 1.754(10) . ?
B7' B12' 1.760(10) . ?
B8' B12' 1.764(10) . ?
B8' B9' 1.786(11) . ?
B9' B12' 1.745(11) . ?
B9' B10' 1.761(11) . ?
B10' B11' 1.732(11) . ?
B10' B12' 1.739(10) . ?
B11' C2' 1.691(9) . ?
B11' B12' 1.745(10) . ?
B3 B8 1.747(9) . ?
B3 B4 1.773(9) . ?
B3 B7 1.779(9) . ?
B4 B5 1.757(9) . ?
B4 B9 1.762(9) . ?
B4 B8 1.773(10) . ?
B5 B10 1.758(10) . ?
B5 B9 1.765(10) . ?
B5 B6 1.780(10) . ?
B6 B11 1.760(10) . ?
B6 B10 1.766(9) . ?
B7 B12 1.742(9) . ?
B7 B11 1.751(10) . ?
B7 B8 1.760(10) . ?
B8 B12 1.748(10) . ?
B8 B9 1.757(10) . ?
B9 B12 1.758(10) . ?
B9 B10 1.787(9) . ?
B10 B11 1.778(10) . ?
B10 B12 1.804(10) . ?
B11 B12 1.775(10) . ?
C1' C2' 1.623(9) . ?
C11' O2" 1.217(8) . ?
C11' O2' 1.237(9) . ?

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
C11' O1' B3' 128.0(5) . . ?
C11 O1 B3 127.3(5) . . ?
C2 C1 B4 111.7(4) . . ?
C2 C1 B5 111.1(4) . . ?
B4 C1 B5 63.4(4) . . ?
C2 C1 B3 61.2(3) . . ?
B4 C1 B3 63.5(4) . . ?
B5 C1 B3 115.7(4) . . ?
C2 C1 B6 61.2(3) . . ?
B4 C1 B6 115.8(4) . . ?
B5 C1 B6 62.9(4) . . ?
B3 C1 B6 114.9(4) . . ?
C1 C2 B7 112.0(4) . . ?
C1 C2 B3 61.8(3) . . ?
B7 C2 B3 63.8(4) . . ?
C1 C2 B11 111.5(4) . . ?
B7 C2 B11 62.6(4) . . ?
B3 C2 B11 115.9(4) . . ?
C1 C2 B6 62.4(3) . . ?
B7 C2 B6 114.8(4) . . ?
B3 C2 B6 116.5(4) . . ?
B11 C2 B6 62.2(4) . . ?
O02 C11 O2 31(2) . . ?
O02 C11 O1 120.5(15) . . ?
O2 C11 O1 124.2(11) . . ?
O02 C11 C12 123.0(16) . . ?
O2 C11 C12 119.3(13) . . ?
O1 C11 C12 113.8(6) . . ?
O1' B3' B4' 128.9(6) . . ?
O1' B3' C1' 117.1(5) . . ?
B4' B3' C1' 57.2(4) . . ?
O1' B3' C2' 115.0(5) . . ?
B4' B3' C2' 101.4(5) . . ?
C1' B3' C2' 55.6(3) . . ?
O1' B3' B8' 134.3(5) . . ?
B4' B3' B8' 60.9(4) . . ?
C1' B3' B8' 104.6(4) . . ?
C2' B3' B8' 103.3(4) . . ?
O1' B3' B7' 123.3(5) . . ?
B4' B3' B7' 106.1(5) . . ?
C1' B3' B7' 102.6(4) . . ?
C2' B3' B7' 57.7(4) . . ?
B8' B3' B7' 59.1(4) . . ?
C1' B4' B5' 58.9(4) . . ?
C1' B4' B3' 61.6(4) . . ?
B5' B4' B3' 110.7(5) . . ?
C1' B4' B9' 106.2(5) . . ?
B5' B4' B9' 59.8(4) . . ?
B3' B4' B9' 110.3(5) . . ?
C1' B4' B8' 107.3(5) . . ?
B5' B4' B8' 109.1(5) . . ?
B3' B4' B8' 60.2(4) . . ?
B9' B4' B8' 61.2(4) . . ?
C1' B5' B4' 58.6(4) . . ?
C1' B5' B9' 106.6(5) . . ?
B4' B5' B9' 60.6(4) . . ?
C1' B5' B6' 60.1(4) . . ?
B4' B5' B6' 108.7(5) . . ?
B9' B5' B6' 109.5(6) . . ?
C1' B5' B10' 106.9(6) . . ?
B4' B5' B10' 108.9(5) . . ?
B9' B5' B10' 60.7(4) . . ?
B6' B5' B10' 60.4(5) . . ?
C2' B6' C1' 57.3(4) . . ?
C2' B6' B5' 103.7(5) . . ?
C1' B6' B5' 58.0(4) . . ?
C2' B6' B11' 59.0(4) . . ?
C1' B6' B11' 105.0(5) . . ?
B5' B6' B11' 106.9(5) . . ?
C2' B6' B10' 104.7(5) . . ?
C1' B6' B10' 105.3(5) . . ?
B5' B6' B10' 60.5(5) . . ?
B11' B6' B10' 59.2(4) . . ?
C2' B7' B8' 106.0(5) . . ?
C2' B7' B11' 58.7(4) . . ?
B8' B7' B11' 108.9(5) . . ?
C2' B7' B12' 104.4(5) . . ?
B8' B7' B12' 60.5(4) . . ?
B11' B7' B12' 59.5(4) . . ?
C2' B7' B3' 60.4(4) . . ?
B8' B7' B3' 60.1(4) . . ?
B11' B7' B3' 109.8(5) . . ?
B12' B7' B3' 108.6(5) . . ?
B7' B8' B3' 60.8(4) . . ?
B7' B8' B12' 60.3(4) . . ?
B3' B8' B12' 109.0(5) . . ?
B7' B8' B4' 105.7(5) . . ?
B3' B8' B4' 58.8(4) . . ?
B12' B8' B4' 105.4(5) . . ?
B7' B8' B9' 106.6(5) . . ?
B3' B8' B9' 107.1(5) . . ?
B12' B8' B9' 58.9(4) . . ?
B4' B8' B9' 58.7(4) . . ?
B5' B9' B4' 59.6(4) . . ?
B5' B9' B12' 107.6(6) . . ?
B4' B9' B12' 107.4(5) . . ?
B5' B9' B10' 60.5(5) . . ?
B4' B9' B10' 108.0(5) . . ?
B12' B9' B10' 59.5(4) . . ?
B5' B9' B8' 108.2(5) . . ?
B4' B9' B8' 60.2(4) . . ?
B12' B9' B8' 59.9(4) . . ?
B10' B9' B8' 108.1(5) . . ?
B11' B10' B12' 60.4(4) . . ?
B11' B10' B6' 60.3(4) . . ?
B12' B10' B6' 108.3(5) . . ?
B11' B10' B5' 106.7(5) . . ?
B12' B10' B5' 106.5(5) . . ?
B6' B10' B5' 59.1(5) . . ?
B11' B10' B9' 107.6(5) . . ?
B12' B10' B9' 59.8(4) . . ?
B6' B10' B9' 106.9(5) . . ?
B5' B10' B9' 58.8(5) . . ?
C2' B11' B10' 105.4(6) . . ?
C2' B11' B12' 105.2(5) . . ?
B10' B11' B12' 60.0(4) . . ?
C2' B11' B6' 58.4(4) . . ?
B10' B11' B6' 60.6(5) . . ?
B12' B11' B6' 108.3(6) . . ?
C2' B11' B7' 58.9(4) . . ?
B10' B11' B7' 108.6(5) . . ?
B12' B11' B7' 60.4(4) . . ?
B6' B11' B7' 108.0(5) . . ?
B10' B12' B9' 60.7(5) . . ?
B10' B12' B11' 59.6(4) . . ?
B9' B12' B11' 107.8(5) . . ?
B10' B12' B7' 108.1(5) . . ?
B9' B12' B7' 107.5(5) . . ?
B11' B12' B7' 60.0(4) . . ?
B10' B12' B8' 110.2(5) . . ?
B9' B12' B8' 61.2(4) . . ?
B11' B12' B8' 108.2(5) . . ?
B7' B12' B8' 59.1(4) . . ?
O1 B3 C2 121.9(5) . . ?
O1 B3 C1 122.7(5) . . ?
C2 B3 C1 57.1(3) . . ?
O1 B3 B8 127.1(5) . . ?
C2 B3 B8 103.5(4) . . ?
C1 B3 B8 103.5(4) . . ?
O1 B3 B4 124.2(5) . . ?
C2 B3 B4 103.3(4) . . ?
C1 B3 B4 57.1(3) . . ?
B8 B3 B4 60.5(4) . . ?
O1 B3 B7 123.3(5) . . ?
C2 B3 B7 57.4(3) . . ?
C1 B3 B7 103.2(4) . . ?
B8 B3 B7 59.9(4) . . ?
B4 B3 B7 107.5(5) . . ?
C1 B4 B5 58.8(4) . . ?
C1 B4 B9 104.8(5) . . ?
B5 B4 B9 60.2(4) . . ?
C1 B4 B8 104.1(5) . . ?
B5 B4 B8 107.6(5) . . ?
B9 B4 B8 59.6(4) . . ?
C1 B4 B3 59.4(3) . . ?
B5 B4 B3 108.6(5) . . ?
B9 B4 B3 107.6(5) . . ?
B8 B4 B3 59.0(4) . . ?
C1 B5 B4 57.8(3) . . ?
C1 B5 B10 105.7(5) . . ?
B4 B5 B10 109.5(5) . . ?
C1 B5 B9 103.9(5) . . ?
B4 B5 B9 60.0(4) . . ?
B10 B5 B9 60.9(4) . . ?
C1 B5 B6 59.8(3) . . ?
B4 B5 B6 108.7(5) . . ?
B10 B5 B6 59.9(4) . . ?
B9 B5 B6 108.2(5) . . ?
C2 B6 C1 56.4(3) . . ?
C2 B6 B11 58.7(3) . . ?
C1 B6 B11 103.9(4) . . ?
C2 B6 B10 104.5(4) . . ?
C1 B6 B10 103.4(4) . . ?
B11 B6 B10 60.6(4) . . ?
C2 B6 B5 102.8(4) . . ?
C1 B6 B5 57.3(3) . . ?
B11 B6 B5 107.3(5) . . ?
B10 B6 B5 59.5(4) . . ?
C2 B7 B12 105.7(5) . . ?
C2 B7 B11 59.5(4) . . ?
B12 B7 B11 61.1(4) . . ?
C2 B7 B8 103.9(5) . . ?
B12 B7 B8 59.9(4) . . ?
B11 B7 B8 108.7(5) . . ?
C2 B7 B3 58.8(3) . . ?
B12 B7 B3 108.1(5) . . ?
B11 B7 B3 109.2(5) . . ?
B8 B7 B3 59.2(4) . . ?
B3 B8 B12 109.2(5) . . ?
B3 B8 B9 108.9(5) . . ?
B12 B8 B9 60.2(4) . . ?
B3 B8 B7 61.0(4) . . ?
B12 B8 B7 59.5(4) . . ?
B9 B8 B7 107.7(5) . . ?
B3 B8 B4 60.5(4) . . ?
B12 B8 B4 108.3(5) . . ?
B9 B8 B4 59.9(4) . . ?
B7 B8 B4 108.3(4) . . ?
B8 B9 B12 59.6(4) . . ?
B8 B9 B4 60.5(4) . . ?
B12 B9 B4 108.3(4) . . ?
B8 B9 B5 107.9(4) . . ?
B12 B9 B5 108.1(5) . . ?
B4 B9 B5 59.8(4) . . ?
B8 B9 B10 108.7(5) . . ?
B12 B9 B10 61.2(4) . . ?
B4 B9 B10 108.0(5) . . ?
B5 B9 B10 59.3(4) . . ?
B5 B10 B6 60.7(4) . . ?
B5 B10 B11 107.5(5) . . ?
B6 B10 B11 59.5(4) . . ?
B5 B10 B9 59.7(4) . . ?
B6 B10 B9 107.9(4) . . ?
B11 B10 B9 106.5(5) . . ?
B5 B10 B12 106.4(5) . . ?
B6 B10 B12 106.9(4) . . ?
B11 B10 B12 59.4(4) . . ?
B9 B10 B12 58.6(4) . . ?
C2 B11 B7 57.9(3) . . ?
C2 B11 B6 59.2(3) . . ?
B7 B11 B6 108.4(5) . . ?
C2 B11 B12 103.0(5) . . ?
B7 B11 B12 59.2(4) . . ?
B6 B11 B12 108.5(5) . . ?
C2 B11 B10 104.3(4) . . ?
B7 B11 B10 108.5(5) . . ?
B6 B11 B10 59.9(4) . . ?
B12 B11 B10 61.0(4) . . ?
B7 B12 B8 60.6(4) . . ?
B7 B12 B9 108.5(5) . . ?
B8 B12 B9 60.2(4) . . ?
B7 B12 B11 59.7(4) . . ?
B8 B12 B11 108.2(4) . . ?
B9 B12 B11 107.8(5) . . ?
B7 B12 B10 107.7(4) . . ?
B8 B12 B10 108.3(5) . . ?
B9 B12 B10 60.2(4) . . ?
B11 B12 B10 59.6(4) . . ?
C2' C1' B4' 109.8(5) . . ?
C2' C1' B5' 109.5(5) . . ?
B4' C1' B5' 62.5(4) . . ?
C2' C1' B6' 60.6(4) . . ?
B4' C1' B6' 113.4(5) . . ?
B5' C1' B6' 62.0(5) . . ?
C2' C1' B3' 62.3(4) . . ?
B4' C1' B3' 61.2(4) . . ?
B5' C1' B3' 113.3(5) . . ?
B6' C1' B3' 114.5(5) . . ?
C1' C2' B6' 62.1(4) . . ?
C1' C2' B11' 111.6(5) . . ?
B6' C2' B11' 62.6(4) . . ?
C1' C2' B7' 111.1(5) . . ?
B6' C2' B7' 114.4(5) . . ?
B11' C2' B7' 62.4(4) . . ?
C1' C2' B3' 62.0(4) . . ?
B6' C2' B3' 115.5(5) . . ?
B11' C2' B3' 114.1(4) . . ?
B7' C2' B3' 61.9(4) . . ?
O2" C11' O2' 59.3(14) . . ?
O2" C11' O1' 114.1(8) . . ?
O2' C11' O1' 115.7(9) . . ?
O2" C11' C12' 121.4(8) . . ?
O2' C11' C12' 119.6(8) . . ?
O1' C11' C12' 115.3(5) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.164
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.071
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1473012'
_audit_update_record             
;
2016-04-08 deposited with the CCDC.
2016-06-08 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 H11 B10 N O2'
_chemical_formula_weight         189.22

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   9.8848(10)
_cell_length_b                   9.8277(10)
_cell_length_c                   20.924(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2032.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    73
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5467
_exptl_absorpt_correction_T_max  0.6842
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13854
_diffrn_reflns_av_R_equivalents  0.1028
_diffrn_reflns_av_sigmaI/netI    0.0627
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         25.25
_reflns_number_total             1842
_reflns_number_gt                1277
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS SHELXTL'

_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)+(0.1154P)²+1.4513P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1842
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.2140
_refine_ls_wR_factor_gt          0.1837
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.5286(3) 0.1822(3) 0.49124(12) 0.0414(7) Uani 1 1 d . . .
C1 C 0.5036(3) 0.1315(3) 0.62070(13) 0.0322(7) Uani 1 1 d . . .
C2 C 0.6480(3) 0.2111(3) 0.60967(13) 0.0315(7) Uani 1 1 d . . .
O1 O 0.6132(2) 0.0931(3) 0.48115(11) 0.0570(7) Uani 1 1 d . . .
O2 O 0.4519(3) 0.2243(3) 0.44980(12) 0.0740(9) Uani 1 1 d . . .
B3 B 0.5170(3) 0.2430(3) 0.55860(15) 0.0305(7) Uani 1 1 d . . .
B4 B 0.3689(3) 0.2357(4) 0.60494(16) 0.0368(8) Uani 1 1 d . . .
H4 H 0.2714 0.2017 0.5852 0.044 Uiso 1 1 calc R . .
B5 B 0.4185(3) 0.1952(3) 0.68452(16) 0.0370(8) Uani 1 1 d . . .
H5 H 0.3522 0.1356 0.7161 0.044 Uiso 1 1 calc R . .
B6 B 0.5970(3) 0.1756(3) 0.68681(15) 0.0364(8) Uani 1 1 d . . .
H6 H 0.6466 0.1030 0.7193 0.044 Uiso 1 1 calc R . .
B7 B 0.6235(3) 0.3754(3) 0.58560(16) 0.0342(8) Uani 1 1 d . . .
H7 H 0.6909 0.4321 0.5533 0.041 Uiso 1 1 calc R . .
B8 B 0.4433(3) 0.3957(4) 0.58402(17) 0.0382(8) Uani 1 1 d . . .
H8 H 0.3936 0.4670 0.5510 0.046 Uiso 1 1 calc R . .
B9 B 0.3818(3) 0.3663(4) 0.66304(18) 0.0416(9) Uani 1 1 d . . .
H9 H 0.2916 0.4193 0.6813 0.050 Uiso 1 1 calc R . .
B10 B 0.5244(4) 0.3282(4) 0.71323(15) 0.0393(8) Uani 1 1 d . . .
H10 H 0.5267 0.3568 0.7641 0.047 Uiso 1 1 calc R . .
B11 B 0.6722(3) 0.3337(3) 0.66525(16) 0.0373(8) Uani 1 1 d . . .
H11 H 0.7714 0.3642 0.6842 0.045 Uiso 1 1 calc R . .
B12 B 0.5394(4) 0.4528(3) 0.65146(17) 0.0400(8) Uani 1 1 d . . .
H12 H 0.5513 0.5617 0.6623 0.048 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
N1 O2 1.224(4) . ?
N1 O1 1.229(3) . ?
N1 B3 1.535(4) . ?
C1 C2 1.644(4) . ?
C1 B5 1.698(4) . ?
C1 B3 1.705(4) . ?
C1 B4 1.712(4) . ?
C1 B6 1.718(4) . ?
C2 B11 1.692(4) . ?
C2 B3 1.708(4) . ?
C2 B7 1.709(4) . ?
C2 B6 1.726(4) . ?
B3 B8 1.752(5) . ?
B3 B4 1.758(4) . ?
B3 B7 1.767(4) . ?
B4 B9 1.773(5) . ?
B4 B5 1.781(5) . ?
B4 B8 1.791(5) . ?
B5 B6 1.775(5) . ?
B5 B9 1.778(5) . ?
B5 B10 1.779(5) . ?
B6 B10 1.753(5) . ?
B6 B11 1.781(5) . ?
B7 B12 1.780(5) . ?
B7 B11 1.782(5) . ?
B7 B8 1.793(4) . ?
B8 B9 1.785(5) . ?
B8 B12 1.791(5) . ?
B9 B12 1.792(5) . ?
B9 B10 1.797(5) . ?
B10 B11 1.774(5) . ?
B10 B12 1.786(5) . ?
B11 B12 1.782(5) . ?

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
O2 N1 O1 122.7(3) . . ?
O2 N1 B3 118.2(3) . . ?
O1 N1 B3 119.1(2) . . ?
C2 C1 B5 111.4(2) . . ?
C2 C1 B3 61.32(17) . . ?
B5 C1 B3 113.7(2) . . ?
C2 C1 B4 111.4(2) . . ?
B5 C1 B4 62.98(19) . . ?
B3 C1 B4 61.92(18) . . ?
C2 C1 B6 61.76(17) . . ?
B5 C1 B6 62.62(19) . . ?
B3 C1 B6 114.2(2) . . ?
B4 C1 B6 115.0(2) . . ?
C1 C2 B11 111.4(2) . . ?
C1 C2 B3 61.10(16) . . ?
B11 C2 B3 114.0(2) . . ?
C1 C2 B7 111.6(2) . . ?
B11 C2 B7 63.21(18) . . ?
B3 C2 B7 62.26(18) . . ?
C1 C2 B6 61.25(17) . . ?
B11 C2 B6 62.79(19) . . ?
B3 C2 B6 113.6(2) . . ?
B7 C2 B6 115.2(2) . . ?
N1 B3 C1 117.1(3) . . ?
N1 B3 C2 116.5(2) . . ?
C1 B3 C2 57.58(16) . . ?
N1 B3 B8 130.0(3) . . ?
C1 B3 B8 106.7(2) . . ?
C2 B3 B8 106.4(2) . . ?
N1 B3 B4 123.6(2) . . ?
C1 B3 B4 59.25(18) . . ?
C2 B3 B4 106.2(2) . . ?
B8 B3 B4 61.4(2) . . ?
N1 B3 B7 122.4(2) . . ?
C1 B3 B7 106.0(2) . . ?
C2 B3 B7 58.91(17) . . ?
B8 B3 B7 61.26(19) . . ?
B4 B3 B7 110.5(2) . . ?
C1 B4 B3 58.83(17) . . ?
C1 B4 B9 104.2(2) . . ?
B3 B4 B9 106.8(2) . . ?
C1 B4 B5 58.11(17) . . ?
B3 B4 B5 107.2(2) . . ?
B9 B4 B5 60.05(19) . . ?
C1 B4 B8 104.6(2) . . ?
B3 B4 B8 59.15(18) . . ?
B9 B4 B8 60.1(2) . . ?
B5 B4 B8 108.2(2) . . ?
C1 B5 B6 59.26(17) . . ?
C1 B5 B9 104.5(2) . . ?
B6 B5 B9 108.2(2) . . ?
C1 B5 B10 104.2(2) . . ?
B6 B5 B10 59.11(19) . . ?
B9 B5 B10 60.69(19) . . ?
C1 B5 B4 58.91(17) . . ?
B6 B5 B4 108.9(2) . . ?
B9 B5 B4 59.7(2) . . ?
B10 B5 B4 108.3(2) . . ?
C1 B6 C2 56.99(16) . . ?
C1 B6 B10 104.4(2) . . ?
C2 B6 B10 104.0(2) . . ?
C1 B6 B5 58.12(17) . . ?
C2 B6 B5 104.1(2) . . ?
B10 B6 B5 60.55(19) . . ?
C1 B6 B11 103.9(2) . . ?
C2 B6 B11 57.65(17) . . ?
B10 B6 B11 60.24(19) . . ?
B5 B6 B11 108.2(2) . . ?
C2 B7 B3 58.83(17) . . ?
C2 B7 B12 104.0(2) . . ?
B3 B7 B12 106.5(2) . . ?
C2 B7 B11 57.91(17) . . ?
B3 B7 B11 106.9(2) . . ?
B12 B7 B11 60.02(19) . . ?
C2 B7 B8 104.6(2) . . ?
B3 B7 B8 58.95(18) . . ?
B12 B7 B8 60.20(19) . . ?
B11 B7 B8 108.1(2) . . ?
B3 B8 B9 106.5(2) . . ?
B3 B8 B4 59.49(19) . . ?
B9 B8 B4 59.43(19) . . ?
B3 B8 B12 106.7(2) . . ?
B9 B8 B12 60.12(19) . . ?
B4 B8 B12 107.5(2) . . ?
B3 B8 B7 59.78(17) . . ?
B9 B8 B7 107.6(2) . . ?
B4 B8 B7 107.8(2) . . ?
B12 B8 B7 59.54(19) . . ?
B4 B9 B5 60.21(19) . . ?
B4 B9 B8 60.4(2) . . ?
B5 B9 B8 108.5(2) . . ?
B4 B9 B12 108.3(2) . . ?
B5 B9 B12 107.8(2) . . ?
B8 B9 B12 60.11(19) . . ?
B4 B9 B10 107.8(2) . . ?
B5 B9 B10 59.67(19) . . ?
B8 B9 B10 107.9(2) . . ?
B12 B9 B10 59.71(19) . . ?
B6 B10 B11 60.66(19) . . ?
B6 B10 B5 60.34(19) . . ?
B11 B10 B5 108.4(2) . . ?
B6 B10 B12 108.9(2) . . ?
B11 B10 B12 60.06(19) . . ?
B5 B10 B12 108.0(2) . . ?
B6 B10 B9 108.4(2) . . ?
B11 B10 B9 108.0(2) . . ?
B5 B10 B9 59.64(19) . . ?
B12 B10 B9 59.99(19) . . ?
C2 B11 B10 104.6(2) . . ?
C2 B11 B6 59.56(18) . . ?
B10 B11 B6 59.10(19) . . ?
C2 B11 B12 104.6(2) . . ?
B10 B11 B12 60.33(19) . . ?
B6 B11 B12 107.9(2) . . ?
C2 B11 B7 58.88(17) . . ?
B10 B11 B7 108.3(2) . . ?
B6 B11 B7 109.0(2) . . ?
B12 B11 B7 59.91(19) . . ?
B7 B12 B11 60.07(18) . . ?
B7 B12 B10 107.8(2) . . ?
B11 B12 B10 59.61(19) . . ?
B7 B12 B8 60.26(18) . . ?
B11 B12 B8 108.2(2) . . ?
B10 B12 B8 108.1(2) . . ?
B7 B12 B9 107.9(2) . . ?
B11 B12 B9 107.9(2) . . ?
B10 B12 B9 60.30(19) . . ?
B8 B12 B9 59.8(2) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.075
#===END


