# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1833050'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-07-27 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            (pin)B-B(aam)
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H18 B2 N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         271.91

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.5677(11)
_cell_length_b                   17.9941(15)
_cell_length_c                   12.3197(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.3700(10)
_cell_angle_gamma                90
_cell_volume                     2967.6(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3437
_cell_measurement_theta_min      2.3607
_cell_measurement_theta_max      23.2156
_cell_measurement_temperature    173.0

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          150.000
_exptl_crystal_size_mid          50.000
_exptl_crystal_size_min          50.000
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152

_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.09
_exptl_absorpt_correction_T_max  0.10

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173.0

_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker Turbo X-ray Source'

_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayered conforcal mirror'

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            12299
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_full        23.25
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             4253
_reflns_number_gt                3268
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1280
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_number_reflns         4253
_refine_ls_number_parameters     369
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0579P)²+1.8782P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.165
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2(Bruker AXS)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'XSHELL V6.3.1(Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.64706(12) 0.44744(9) 0.73296(13) 0.0362(4) Uani d . . . 1 . .
O O4 0.09111(11) 0.55778(9) 0.26156(14) 0.0371(4) Uani d . . . 1 . .
O O2 0.52043(12) 0.36989(9) 0.66189(14) 0.0376(4) Uani d . . . 1 . .
O O5 -0.03264(12) 0.47138(9) 0.22864(15) 0.0415(5) Uani d . . . 1 . .
O O6 0.40321(12) 0.36551(11) 0.37400(15) 0.0477(5) Uani d . . . 1 . .
O O3 0.91675(12) 0.36735(12) 0.47091(15) 0.0498(5) Uani d . . . 1 . .
N N2 0.61360(13) 0.34995(11) 0.44360(15) 0.0296(5) Uani d . . . 1 . .
N N3 0.24970(14) 0.41829(11) 0.33376(16) 0.0328(5) Uani d . . . 1 . .
N N4 0.10686(14) 0.36298(11) 0.39867(16) 0.0324(5) Uani d . . . 1 . .
N N1 0.77589(14) 0.38221(11) 0.54632(16) 0.0329(5) Uani d . . . 1 . .
C C1 0.65762(17) 0.33434(13) 0.35189(19) 0.0283(6) Uani d . . . 1 . .
C C2 0.76153(16) 0.34198(13) 0.35725(19) 0.0298(6) Uani d . . . 1 . .
C C3 0.27266(17) 0.31241(13) 0.45626(19) 0.0301(6) Uani d . . . 1 . .
C C4 0.16985(17) 0.31233(13) 0.46076(19) 0.0302(6) Uani d . . . 1 . .
C C5 0.31472(17) 0.36602(15) 0.3859(2) 0.0345(6) Uani d . . . 1 . .
C C6 0.82470(17) 0.36458(14) 0.4602(2) 0.0337(6) Uani d . . . 1 . .
C C7 0.60002(18) 0.31096(13) 0.2532(2) 0.0342(6) Uani d . . . 1 . .
H H7 0.5299 0.3048 0.2488 0.041 Uiso calc U . R 1 . .
C C8 0.13251(19) 0.26166(14) 0.5301(2) 0.0374(6) Uani d . . . 1 . .
H H8 0.0629 0.2605 0.5327 0.045 Uiso calc U . R 1 . .
C C9 0.33523(19) 0.26273(15) 0.5217(2) 0.0401(7) Uani d . . . 1 . .
H H9 0.4047 0.2625 0.5187 0.048 Uiso calc U . R 1 . .
C C10 0.6440(2) 0.29684(14) 0.1626(2) 0.0398(7) Uani d . . . 1 . .
H H10 0.6041 0.2806 0.0962 0.048 Uiso calc U . R 1 . .
C C11 0.00548(18) 0.59594(15) 0.1958(2) 0.0381(6) Uani d . . . 1 . .
C C12 0.80404(19) 0.32833(15) 0.2632(2) 0.0386(6) Uani d . . . 1 . .
H H12 0.8739 0.3346 0.266 0.046 Uiso calc U . R 1 . .
C C13 0.5806(2) 0.44357(14) 0.8156(2) 0.0381(6) Uani d . . . 1 . .
C C14 0.48316(19) 0.41275(14) 0.7480(2) 0.0392(6) Uani d . . . 1 . .
C C15 -0.08216(18) 0.54415(15) 0.2116(2) 0.0398(6) Uani d . . . 1 . .
C C16 0.2973(2) 0.21404(15) 0.5907(2) 0.0453(7) Uani d . . . 1 . .
H H16 0.3405 0.1808 0.6357 0.054 Uiso calc U . R 1 . .
C C17 0.7462(2) 0.30598(15) 0.1668(2) 0.0435(7) Uani d . . . 1 . .
H H17 0.7759 0.2968 0.1034 0.052 Uiso calc U . R 1 . .
C C18 0.1953(2) 0.21383(15) 0.5940(2) 0.0443(7) Uani d . . . 1 . .
H H18 0.1689 0.1801 0.6412 0.053 Uiso calc U . R 1 . .
C C19 0.0280(2) 0.59854(17) 0.0794(2) 0.0512(8) Uani d . . . 1 . .
H H19A 0.0902 0.6261 0.0785 0.077 Uiso calc U . R 1 . .
H H19B -0.0269 0.6233 0.0315 0.077 Uiso calc U . R 1 . .
H H19C 0.0355 0.5478 0.053 0.077 Uiso calc U . R 1 . .
B B2 0.6114(2) 0.39847(16) 0.6507(2) 0.0308(7) Uani d . . . 1 . .
C C20 -0.1656(2) 0.53827(17) 0.1131(2) 0.0532(8) Uani d . . . 1 . .
H H20A -0.1379 0.521 0.0488 0.08 Uiso calc U . R 1 . .
H H20B -0.1965 0.5871 0.0975 0.08 Uiso calc U . R 1 . .
H H20C -0.216 0.5028 0.1296 0.08 Uiso calc U . R 1 . .
C C21 0.5721(2) 0.52084(15) 0.8623(2) 0.0527(8) Uani d . . . 1 . .
H H21A 0.636 0.5349 0.9066 0.079 Uiso calc U . R 1 . .
H H21B 0.5198 0.5212 0.9085 0.079 Uiso calc U . R 1 . .
H H21C 0.555 0.5564 0.8018 0.079 Uiso calc U . R 1 . .
C C22 -0.0010(2) 0.67366(15) 0.2407(2) 0.0497(7) Uani d . . . 1 . .
H H22A -0.0022 0.6711 0.32 0.075 Uiso calc U . R 1 . .
H H22B -0.0622 0.6977 0.2037 0.075 Uiso calc U . R 1 . .
H H22C 0.0572 0.7025 0.2276 0.075 Uiso calc U . R 1 . .
B B1 0.6695(2) 0.37606(15) 0.5429(2) 0.0303(6) Uani d . . . 1 . .
C C23 0.4158(2) 0.47223(17) 0.6885(3) 0.0547(8) Uani d . . . 1 . .
H H23A 0.4552 0.5052 0.6488 0.082 Uiso calc U . R 1 . .
H H23B 0.3859 0.5012 0.7421 0.082 Uiso calc U . R 1 . .
H H23C 0.3629 0.4487 0.6361 0.082 Uiso calc U . R 1 . .
B B3 0.1437(2) 0.41946(16) 0.3363(2) 0.0326(7) Uani d . . . 1 . .
C C24 -0.1252(2) 0.55953(17) 0.3150(2) 0.0511(8) Uani d . . . 1 . .
H H24A -0.169 0.5184 0.3285 0.077 Uiso calc U . R 1 . .
H H24B -0.1637 0.6058 0.3061 0.077 Uiso calc U . R 1 . .
H H24C -0.0708 0.5643 0.3775 0.077 Uiso calc U . R 1 . .
B B4 0.0654(2) 0.48476(17) 0.2715(2) 0.0343(7) Uani d . . . 1 . .
C C25 0.4240(2) 0.36077(17) 0.8105(3) 0.0585(9) Uani d . . . 1 . .
H H25A 0.3646 0.3431 0.7611 0.088 Uiso calc U . R 1 . .
H H25B 0.4034 0.3875 0.8724 0.088 Uiso calc U . R 1 . .
H H25C 0.4658 0.3182 0.8382 0.088 Uiso calc U . R 1 . .
C C26 0.6304(2) 0.39114(18) 0.9044(2) 0.0579(8) Uani d . . . 1 . .
H H26A 0.6336 0.3412 0.8735 0.087 Uiso calc U . R 1 . .
H H26B 0.5916 0.3896 0.9648 0.087 Uiso calc U . R 1 . .
H H26C 0.6982 0.4087 0.9322 0.087 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 B2 . 1.370(3) ?
O1 C13 . 1.467(3) ?
O4 B4 . 1.370(3) ?
O4 C11 . 1.474(3) ?
O2 B2 . 1.364(3) ?
O2 C14 . 1.466(3) ?
O5 B4 . 1.370(3) ?
O5 C15 . 1.471(3) ?
O6 C5 . 1.233(3) ?
O3 C6 . 1.235(3) ?
N2 C1 . 1.390(3) ?
N2 B1 . 1.411(3) ?
N3 C5 . 1.375(3) ?
N3 B3 . 1.443(3) ?
N4 C4 . 1.390(3) ?
N4 B3 . 1.414(4) ?
N1 C6 . 1.376(3) ?
N1 B1 . 1.441(3) ?
C1 C7 . 1.399(3) ?
C1 C2 . 1.407(3) ?
C2 C12 . 1.398(3) ?
C2 C6 . 1.468(3) ?
C3 C9 . 1.395(3) ?
C3 C4 . 1.405(3) ?
C3 C5 . 1.473(3) ?
C4 C8 . 1.399(3) ?
C7 C10 . 1.372(3) ?
C7 H7 . 0.95 ?
C8 C18 . 1.367(4) ?
C8 H8 . 0.95 ?
C9 C16 . 1.377(4) ?
C9 H9 . 0.95 ?
C10 C17 . 1.389(4) ?
C10 H10 . 0.95 ?
C11 C22 . 1.512(4) ?
C11 C19 . 1.514(4) ?
C11 C15 . 1.548(4) ?
C12 C17 . 1.372(4) ?
C12 H12 . 0.95 ?
C13 C21 . 1.516(4) ?
C13 C26 . 1.517(4) ?
C13 C14 . 1.546(4) ?
C14 C23 . 1.516(4) ?
C14 C25 . 1.521(4) ?
C15 C24 . 1.512(4) ?
C15 C20 . 1.522(4) ?
C16 C18 . 1.392(4) ?
C16 H16 . 0.95 ?
C17 H17 . 0.95 ?
C18 H18 . 0.95 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
B2 B1 . 1.700(4) ?
C20 H20A . 0.98 ?
C20 H20B . 0.98 ?
C20 H20C . 0.98 ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
C23 H23A . 0.98 ?
C23 H23B . 0.98 ?
C23 H23C . 0.98 ?
B3 B4 . 1.695(4) ?
C24 H24A . 0.98 ?
C24 H24B . 0.98 ?
C24 H24C . 0.98 ?
C25 H25A . 0.98 ?
C25 H25B . 0.98 ?
C25 H25C . 0.98 ?
C26 H26A . 0.98 ?
C26 H26B . 0.98 ?
C26 H26C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
B2 O1 C13 . . 107.43(19) ?
B4 O4 C11 . . 107.85(19) ?
B2 O2 C14 . . 107.38(19) ?
B4 O5 C15 . . 106.91(19) ?
C1 N2 B1 . . 122.06(19) ?
C5 N3 B3 . . 124.4(2) ?
C4 N4 B3 . . 122.0(2) ?
C6 N1 B1 . . 124.4(2) ?
N2 C1 C7 . . 120.9(2) ?
N2 C1 C2 . . 120.1(2) ?
C7 C1 C2 . . 118.9(2) ?
C12 C2 C1 . . 119.3(2) ?
C12 C2 C6 . . 120.2(2) ?
C1 C2 C6 . . 120.5(2) ?
C9 C3 C4 . . 119.4(2) ?
C9 C3 C5 . . 120.2(2) ?
C4 C3 C5 . . 120.4(2) ?
N4 C4 C8 . . 120.8(2) ?
N4 C4 C3 . . 120.2(2) ?
C8 C4 C3 . . 119.0(2) ?
O6 C5 N3 . . 120.9(2) ?
O6 C5 C3 . . 122.9(2) ?
N3 C5 C3 . . 116.2(2) ?
O3 C6 N1 . . 120.9(2) ?
O3 C6 C2 . . 122.8(2) ?
N1 C6 C2 . . 116.3(2) ?
C10 C7 C1 . . 120.5(2) ?
C10 C7 H7 . . 119.8 ?
C1 C7 H7 . . 119.8 ?
C18 C8 C4 . . 120.6(2) ?
C18 C8 H8 . . 119.7 ?
C4 C8 H8 . . 119.7 ?
C16 C9 C3 . . 120.7(2) ?
C16 C9 H9 . . 119.6 ?
C3 C9 H9 . . 119.6 ?
C7 C10 C17 . . 120.8(2) ?
C7 C10 H10 . . 119.6 ?
C17 C10 H10 . . 119.6 ?
O4 C11 C22 . . 108.5(2) ?
O4 C11 C19 . . 105.8(2) ?
C22 C11 C19 . . 110.6(2) ?
O4 C11 C15 . . 101.72(19) ?
C22 C11 C15 . . 114.8(2) ?
C19 C11 C15 . . 114.6(2) ?
C17 C12 C2 . . 120.9(2) ?
C17 C12 H12 . . 119.5 ?
C2 C12 H12 . . 119.5 ?
O1 C13 C21 . . 108.2(2) ?
O1 C13 C26 . . 106.1(2) ?
C21 C13 C26 . . 110.5(2) ?
O1 C13 C14 . . 102.19(18) ?
C21 C13 C14 . . 114.9(2) ?
C26 C13 C14 . . 114.0(2) ?
O2 C14 C23 . . 105.8(2) ?
O2 C14 C25 . . 108.4(2) ?
C23 C14 C25 . . 110.6(2) ?
O2 C14 C13 . . 102.30(18) ?
C23 C14 C13 . . 113.7(2) ?
C25 C14 C13 . . 115.0(2) ?
O5 C15 C24 . . 105.8(2) ?
O5 C15 C20 . . 108.4(2) ?
C24 C15 C20 . . 110.2(2) ?
O5 C15 C11 . . 102.22(18) ?
C24 C15 C11 . . 114.0(2) ?
C20 C15 C11 . . 115.3(2) ?
C9 C16 C18 . . 119.5(3) ?
C9 C16 H16 . . 120.2 ?
C18 C16 H16 . . 120.2 ?
C12 C17 C10 . . 119.6(2) ?
C12 C17 H17 . . 120.2 ?
C10 C17 H17 . . 120.2 ?
C8 C18 C16 . . 120.7(3) ?
C8 C18 H18 . . 119.6 ?
C16 C18 H18 . . 119.6 ?
C11 C19 H19A . . 109.5 ?
C11 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C11 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
O2 B2 O1 . . 112.6(2) ?
O2 B2 B1 . . 122.1(2) ?
O1 B2 B1 . . 125.2(2) ?
C15 C20 H20A . . 109.5 ?
C15 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C15 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C13 C21 H21A . . 109.5 ?
C13 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C13 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C11 C22 H22A . . 109.5 ?
C11 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C11 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
N2 B1 N1 . . 116.4(2) ?
N2 B1 B2 . . 120.3(2) ?
N1 B1 B2 . . 123.3(2) ?
C14 C23 H23A . . 109.5 ?
C14 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C14 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
N4 B3 N3 . . 116.3(2) ?
N4 B3 B4 . . 120.3(2) ?
N3 B3 B4 . . 123.4(2) ?
C15 C24 H24A . . 109.5 ?
C15 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C15 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
O5 B4 O4 . . 112.3(2) ?
O5 B4 B3 . . 123.7(2) ?
O4 B4 B3 . . 123.9(2) ?
C14 C25 H25A . . 109.5 ?
C14 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C14 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
C13 C26 H26A . . 109.5 ?
C13 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C13 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?

####################################################################### 
# 
# 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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1833053'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-07-27 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            (pin)B-B(dan)
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H20 B2 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         293.96

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.217(5)
_cell_length_b                   11.608(5)
_cell_length_c                   10.778(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.985(6)
_cell_angle_gamma                90
_cell_volume                     1611.3(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2975
_cell_measurement_theta_min      2.3635
_cell_measurement_theta_max      27.0788
_cell_measurement_temperature    173

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          200.000
_exptl_crystal_size_mid          200.000
_exptl_crystal_size_min          200.000
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624

_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.02
_exptl_absorpt_correction_T_max  0.02

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173

_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker Turbo X-ray Source'

_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayered conforcal mirror'

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            8224
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         27.18
_diffrn_reflns_theta_full        27.18
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12

_refine_special_details          
;
;

_reflns_number_total             3529
_reflns_number_gt                2674
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1331
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_number_reflns         3529
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0647P)²+0.5880P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.218
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2(Bruker AXS)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSHELL V6.3.1(Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.41786(13) 0.76812(14) 0.46402(17) 0.0305(4) Uani d . . . 1 . .
B B2 0.30224(14) 0.70521(14) 0.39167(17) 0.0309(4) Uani d . . . 1 . .
C C1 0.60837(11) 0.87290(12) 0.59248(14) 0.0282(3) Uani d . . . 1 . .
C C2 0.60900(12) 0.79213(12) 0.49221(15) 0.0293(3) Uani d . . . 1 . .
C C3 0.51416(12) 0.90221(12) 0.62904(15) 0.0292(3) Uani d . . . 1 . .
C C4 0.70439(12) 0.92532(13) 0.65678(15) 0.0338(4) Uani d . . . 1 . .
C C5 0.12839(12) 0.66204(14) 0.35157(15) 0.0339(4) Uani d . . . 1 . .
C C6 0.18265(12) 0.58606(13) 0.26662(16) 0.0340(4) Uani d . . . 1 . .
C C7 0.51508(14) 0.98306(13) 0.72483(16) 0.0364(4) Uani d . . . 1 . .
C C8 0.70114(13) 0.76583(14) 0.45731(18) 0.0374(4) Uani d . . . 1 . .
C C9 0.70161(15) 1.00714(14) 0.75478(17) 0.0417(4) Uani d . . . 1 . .
C C10 0.79678(13) 0.89446(16) 0.61985(19) 0.0420(4) Uani d . . . 1 . .
C C11 0.79522(14) 0.81668(16) 0.52293(19) 0.0442(4) Uani d . . . 1 . .
C C12 0.61010(16) 1.03451(14) 0.78649(17) 0.0432(4) Uani d . . . 1 . .
C C13 0.12731(17) 0.58338(18) 0.12662(18) 0.0459(5) Uani d . . . 1 . .
C C14 0.05942(17) 0.5960(2) 0.4225(2) 0.0523(5) Uani d . . . 1 . .
C C15 0.06960(15) 0.76517(17) 0.2818(2) 0.0458(5) Uani d . . . 1 . .
C C16 0.20740(18) 0.46389(16) 0.3175(2) 0.0539(5) Uani d . . . 1 . .
N N1 0.51369(10) 0.74274(11) 0.43137(14) 0.0322(3) Uani d . . . 1 . .
N N2 0.42224(10) 0.84767(11) 0.56582(13) 0.0312(3) Uani d . . . 1 . .
O O1 0.28358(8) 0.64428(9) 0.27932(11) 0.0356(3) Uani d . . . 1 . .
O O2 0.21726(8) 0.70879(10) 0.44493(11) 0.0360(3) Uani d . . . 1 . .
H H8 0.7012(15) 0.7098(17) 0.3865(19) 0.043(5) Uiso d . . . 1 . .
H H11 0.8630(16) 0.7993(17) 0.496(2) 0.049(5) Uiso d . . . 1 . .
H H10 0.8635(16) 0.9271(18) 0.666(2) 0.055(6) Uiso d . . . 1 . .
H H9 0.7697(16) 1.0405(17) 0.7979(19) 0.049(5) Uiso d . . . 1 . .
H H12 0.6087(15) 1.0906(18) 0.855(2) 0.053(6) Uiso d . . . 1 . .
H H7 0.4471(14) 1.0015(16) 0.7497(18) 0.041(5) Uiso d . . . 1 . .
H H1N 0.5176(16) 0.6965(19) 0.367(2) 0.053(6) Uiso d . . . 1 . .
H H2N 0.3652(14) 0.8607(15) 0.5958(17) 0.033(5) Uiso d . . . 1 . .
H H14A 0.0018(17) 0.5554(19) 0.360(2) 0.059(6) Uiso d . . . 1 . .
H H14B 0.103(2) 0.536(2) 0.484(3) 0.080(8) Uiso d . . . 1 . .
H H14C 0.0261(19) 0.645(2) 0.476(2) 0.074(7) Uiso d . . . 1 . .
H H15A 0.1158(17) 0.8021(19) 0.232(2) 0.055(6) Uiso d . . . 1 . .
H H15B 0.0048(17) 0.7427(19) 0.222(2) 0.054(6) Uiso d . . . 1 . .
H H15C 0.0455(18) 0.820(2) 0.349(2) 0.069(7) Uiso d . . . 1 . .
H H13A 0.0548(16) 0.5507(18) 0.1176(19) 0.053(6) Uiso d . . . 1 . .
H H13B 0.1694(16) 0.5379(19) 0.083(2) 0.054(6) Uiso d . . . 1 . .
H H13C 0.1230(17) 0.665(2) 0.083(2) 0.063(6) Uiso d . . . 1 . .
H H16A 0.1407(17) 0.420(2) 0.308(2) 0.058(6) Uiso d . . . 1 . .
H H16B 0.2426(17) 0.4651(19) 0.411(2) 0.060(6) Uiso d . . . 1 . .
H H16C 0.2563(19) 0.426(2) 0.270(2) 0.069(7) Uiso d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 N1 . 1.420(2) ?
B1 N2 . 1.425(2) ?
B1 B2 . 1.715(2) ?
B2 O2 . 1.372(2) ?
B2 O1 . 1.376(2) ?
C1 C3 . 1.429(2) ?
C1 C4 . 1.437(2) ?
C1 C2 . 1.432(2) ?
C2 C8 . 1.387(2) ?
C2 N1 . 1.405(2) ?
C3 C7 . 1.393(2) ?
C3 N2 . 1.403(2) ?
C4 C10 . 1.413(3) ?
C4 C9 . 1.427(3) ?
C5 O2 . 1.4683(18) ?
C5 C14 . 1.522(2) ?
C5 C15 . 1.530(3) ?
C5 C6 . 1.557(2) ?
C6 O1 . 1.4742(19) ?
C6 C13 . 1.522(3) ?
C6 C16 . 1.529(2) ?
C7 C12 . 1.414(3) ?
C7 H7 . 1.016(19) ?
C8 C11 . 1.414(3) ?
C8 H8 . 1.00(2) ?
C9 C12 . 1.366(3) ?
C9 H9 . 0.99(2) ?
C10 C11 . 1.377(3) ?
C10 H10 . 0.98(2) ?
C11 H11 . 1.02(2) ?
C12 H12 . 0.99(2) ?
C13 H13A . 1.01(2) ?
C13 H13B . 0.96(2) ?
C13 H13C . 1.05(2) ?
C14 H14A . 1.01(2) ?
C14 H14B . 1.05(3) ?
C14 H14C . 0.99(3) ?
C15 H15A . 1.00(2) ?
C15 H15B . 0.98(2) ?
C15 H15C . 1.06(2) ?
C16 H16A . 1.00(2) ?
C16 H16B . 1.01(2) ?
C16 H16C . 1.01(3) ?
N1 H1N . 0.89(2) ?
N2 H2N . 0.898(18) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 B1 N2 . . 116.17(14) ?
N1 B1 B2 . . 123.54(15) ?
N2 B1 B2 . . 120.26(14) ?
O2 B2 O1 . . 112.46(13) ?
O2 B2 B1 . . 121.76(15) ?
O1 B2 B1 . . 125.75(15) ?
C3 C1 C4 . . 119.73(14) ?
C3 C1 C2 . . 121.14(13) ?
C4 C1 C2 . . 119.13(14) ?
C8 C2 N1 . . 122.23(15) ?
C8 C2 C1 . . 120.21(14) ?
N1 C2 C1 . . 117.55(14) ?
C7 C3 N2 . . 121.75(15) ?
C7 C3 C1 . . 120.11(14) ?
N2 C3 C1 . . 118.15(14) ?
C10 C4 C9 . . 123.02(15) ?
C10 C4 C1 . . 118.83(16) ?
C9 C4 C1 . . 118.16(16) ?
O2 C5 C14 . . 108.60(14) ?
O2 C5 C15 . . 106.72(13) ?
C14 C5 C15 . . 110.22(17) ?
O2 C5 C6 . . 102.06(12) ?
C14 C5 C6 . . 114.66(15) ?
C15 C5 C6 . . 113.84(15) ?
O1 C6 C13 . . 108.94(14) ?
O1 C6 C16 . . 106.00(14) ?
C13 C6 C16 . . 110.66(15) ?
O1 C6 C5 . . 102.27(11) ?
C13 C6 C5 . . 114.34(15) ?
C16 C6 C5 . . 113.84(16) ?
C3 C7 C12 . . 119.44(17) ?
C3 C7 H7 . . 118.4(11) ?
C12 C7 H7 . . 122.1(11) ?
C2 C8 C11 . . 119.97(17) ?
C2 C8 H8 . . 120.0(11) ?
C11 C8 H8 . . 120.0(11) ?
C12 C9 C4 . . 120.75(15) ?
C12 C9 H9 . . 123.5(12) ?
C4 C9 H9 . . 115.7(12) ?
C11 C10 C4 . . 120.88(16) ?
C11 C10 H10 . . 119.4(13) ?
C4 C10 H10 . . 119.7(13) ?
C10 C11 C8 . . 120.96(17) ?
C10 C11 H11 . . 118.7(12) ?
C8 C11 H11 . . 120.3(12) ?
C9 C12 C7 . . 121.79(17) ?
C9 C12 H12 . . 120.4(12) ?
C7 C12 H12 . . 117.8(12) ?
C6 C13 H13A . . 109.6(12) ?
C6 C13 H13B . . 107.2(13) ?
H13A C13 H13B . . 112.6(17) ?
C6 C13 H13C . . 112.8(12) ?
H13A C13 H13C . . 109.8(17) ?
H13B C13 H13C . . 104.7(18) ?
C5 C14 H14A . . 110.3(13) ?
C5 C14 H14B . . 110.3(14) ?
H14A C14 H14B . . 109.6(19) ?
C5 C14 H14C . . 113.5(15) ?
H14A C14 H14C . . 107.0(19) ?
H14B C14 H14C . . 106.(2) ?
C5 C15 H15A . . 107.3(13) ?
C5 C15 H15B . . 112.7(13) ?
H15A C15 H15B . . 108.0(18) ?
C5 C15 H15C . . 109.4(13) ?
H15A C15 H15C . . 114.9(18) ?
H15B C15 H15C . . 104.7(17) ?
C6 C16 H16A . . 108.8(12) ?
C6 C16 H16B . . 111.0(13) ?
H16A C16 H16B . . 107.6(18) ?
C6 C16 H16C . . 109.6(14) ?
H16A C16 H16C . . 112.1(19) ?
H16B C16 H16C . . 107.8(18) ?
C2 N1 B1 . . 123.78(14) ?
C2 N1 H1N . . 114.0(14) ?
B1 N1 H1N . . 122.1(14) ?
C3 N2 B1 . . 123.17(14) ?
C3 N2 H2N . . 117.0(11) ?
B1 N2 H2N . . 119.6(11) ?
B2 O1 C6 . . 107.27(12) ?
B2 O2 C5 . . 107.82(12) ?

