# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_d1574
_audit_block_doi                 10.5517/ccdc.csd.cc1nqjkg
_database_code_depnum_ccdc_archive 'CCDC 1540996'
_audit_update_record             
;
2017-03-29 deposited with the CCDC.
2017-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        D1574
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H21 B N2 O5, C2 H3 N'
_chemical_formula_sum            'C15 H24 B N3 O5'
_chemical_formula_weight         337.18

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'
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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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                   9.8379(6)
_cell_length_b                   14.0414(8)
_cell_length_c                   12.8082(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.623(3)
_cell_angle_gamma                90
_cell_volume                     1749.30(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    147(2)
_cell_measurement_reflns_used    9925
_cell_measurement_theta_min      4.55
_cell_measurement_theta_max      66.61

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.788
_shelx_estimated_absorpt_T_min   0.878
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6911
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      147(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33599
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.546
_diffrn_reflns_theta_max         67.265
_diffrn_reflns_theta_full        67.265
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3091
_reflns_number_gt                2853
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXT (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0394P)²+0.5622P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3091
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0824
_refine_ls_wR_factor_gt          0.0805
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.70939(8) 0.99113(5) 0.39317(6) 0.02236(18) Uani 1 1 d . . . . .
O2 O 0.53444(9) 1.08567(6) 0.41861(7) 0.0337(2) Uani 1 1 d . . . . .
O3 O 0.82320(8) 0.83709(5) 0.38881(6) 0.02375(19) Uani 1 1 d . . . . .
O4 O 0.79900(10) 0.71729(6) 0.50044(7) 0.0363(2) Uani 1 1 d . . . . .
O5 O 0.54077(10) 1.09479(6) 0.06606(7) 0.0374(2) Uani 1 1 d . . . . .
H5O H 0.470(2) 1.0729(14) 0.0114(15) 0.063(5) Uiso 1 1 d . . . . .
N1 N 0.58414(9) 0.85774(6) 0.31223(7) 0.0215(2) Uani 1 1 d . . . . .
N2 N 0.61521(10) 1.00933(7) 0.09338(8) 0.0261(2) Uani 1 1 d . . . . .
C1 C 0.48931(12) 0.93892(8) 0.32137(10) 0.0262(3) Uani 1 1 d . . . . .
H1A H 0.4129 0.9193 0.3589 0.031 Uiso 1 1 calc R U . . .
H1B H 0.4504 0.9634 0.2507 0.031 Uiso 1 1 calc R U . . .
C2 C 0.57778(12) 1.01372(8) 0.38388(9) 0.0244(3) Uani 1 1 d . . . . .
C3 C 0.59823(13) 0.79464(8) 0.40766(9) 0.0265(3) Uani 1 1 d . . . . .
H3A H 0.5486 0.7339 0.3909 0.032 Uiso 1 1 calc R U . . .
H3B H 0.5601 0.8263 0.4660 0.032 Uiso 1 1 calc R U . . .
C4 C 0.74964(13) 0.77676(8) 0.43836(9) 0.0252(3) Uani 1 1 d . . . . .
C5 C 0.54338(13) 0.80009(8) 0.21456(9) 0.0280(3) Uani 1 1 d . . . . .
H5A H 0.4544 0.7696 0.2175 0.042 Uiso 1 1 calc R U . . .
H5B H 0.6131 0.7511 0.2095 0.042 Uiso 1 1 calc R U . . .
H5C H 0.5359 0.8417 0.1526 0.042 Uiso 1 1 calc R U . . .
C6 C 0.79355(11) 0.93874(7) 0.21973(8) 0.0194(2) Uani 1 1 d . . . . .
H6A H 0.7787 0.8840 0.1693 0.023 Uiso 1 1 calc R U . . .
C7 C 0.94987(11) 0.96130(8) 0.23919(8) 0.0203(2) Uani 1 1 d . . . . .
H7A H 0.9980 0.9019 0.2677 0.024 Uiso 1 1 calc R U . . .
C8 C 1.00156(12) 0.98427(9) 0.13513(9) 0.0250(3) Uani 1 1 d . . . . .
H8A H 0.9797 0.9304 0.0855 0.030 Uiso 1 1 calc R U . . .
H8B H 0.9531 1.0414 0.1031 0.030 Uiso 1 1 calc R U . . .
C9 C 1.15625(12) 1.00239(9) 0.15092(9) 0.0288(3) Uani 1 1 d . . . . .
H9A H 1.2056 0.9434 0.1763 0.035 Uiso 1 1 calc R U . . .
H9B H 1.1848 1.0201 0.0826 0.035 Uiso 1 1 calc R U . . .
C10 C 1.19427(13) 1.08201(9) 0.23074(10) 0.0296(3) Uani 1 1 d . . . . .
H10A H 1.2952 1.0909 0.2423 0.036 Uiso 1 1 calc R U . . .
H10B H 1.1514 1.1423 0.2023 0.036 Uiso 1 1 calc R U . . .
C11 C 1.14615(12) 1.05912(9) 0.33530(9) 0.0304(3) Uani 1 1 d . . . . .
H11A H 1.1684 1.1131 0.3846 0.036 Uiso 1 1 calc R U . . .
H11B H 1.1957 1.0022 0.3669 0.036 Uiso 1 1 calc R U . . .
C12 C 0.99134(12) 1.04032(9) 0.32049(9) 0.0266(3) Uani 1 1 d . . . . .
H12A H 0.9416 1.0996 0.2968 0.032 Uiso 1 1 calc R U . . .
H12B H 0.9643 1.0216 0.3890 0.032 Uiso 1 1 calc R U . . .
C13 C 0.71009(11) 1.02101(8) 0.17111(8) 0.0220(2) Uani 1 1 d . . . . .
H13A H 0.7285 1.0831 0.1990 0.026 Uiso 1 1 calc R U . . .
B1 B 0.73765(12) 0.90786(9) 0.32630(9) 0.0193(3) Uani 1 1 d . . . . .
N1S N 0.23374(14) 0.77258(9) 0.32491(13) 0.0537(3) Uani 1 1 d . . . . .
C1S C 0.20107(14) 0.76871(10) 0.40626(13) 0.0407(3) Uani 1 1 d . . . . .
C2S C 0.16036(19) 0.76408(14) 0.51035(14) 0.0607(5) Uani 1 1 d . . . . .
H2S1 H 0.1933 0.8210 0.5507 0.091 Uiso 1 1 calc R U . . .
H2S2 H 0.2004 0.7072 0.5472 0.091 Uiso 1 1 calc R U . . .
H2S3 H 0.0599 0.7609 0.5035 0.091 Uiso 1 1 calc R U . . .


_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 C2 1.3210(14) . ?
O1 B1 1.4997(14) . ?
O2 C2 1.2071(14) . ?
O3 C4 1.3347(14) . ?
O3 B1 1.4612(14) . ?
O4 C4 1.2041(14) . ?
O5 N2 1.4219(12) . ?
O5 H5O 0.96(2) . ?
N1 C1 1.4886(14) . ?
N1 C5 1.4935(14) . ?
N1 C3 1.4992(14) . ?
N1 B1 1.6514(15) . ?
N2 C13 1.2691(15) . ?
C1 C2 1.5142(16) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C3 C4 1.5035(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C13 1.4976(15) . ?
C6 C7 1.5532(15) . ?
C6 B1 1.6058(15) . ?
C6 H6A 1.0000 . ?
C7 C8 1.5305(15) . ?
C7 C12 1.5345(15) . ?
C7 H7A 1.0000 . ?
C8 C9 1.5262(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5233(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5202(17) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5292(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9500 . ?
N1S C1S 1.137(2) . ?
C1S C2S 1.450(2) . ?
C2S H2S1 0.9800 . ?
C2S H2S2 0.9800 . ?
C2S H2S3 0.9800 . ?

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
C2 O1 B1 113.51(9) . . ?
C4 O3 B1 112.54(9) . . ?
N2 O5 H5O 101.5(11) . . ?
C1 N1 C5 112.84(9) . . ?
C1 N1 C3 111.77(9) . . ?
C5 N1 C3 110.06(9) . . ?
C1 N1 B1 103.81(8) . . ?
C5 N1 B1 116.66(8) . . ?
C3 N1 B1 101.05(8) . . ?
C13 N2 O5 112.03(9) . . ?
N1 C1 C2 104.80(9) . . ?
N1 C1 H1A 110.8 . . ?
C2 C1 H1A 110.8 . . ?
N1 C1 H1B 110.8 . . ?
C2 C1 H1B 110.8 . . ?
H1A C1 H1B 108.9 . . ?
O2 C2 O1 124.29(11) . . ?
O2 C2 C1 124.65(11) . . ?
O1 C2 C1 111.04(9) . . ?
N1 C3 C4 106.19(9) . . ?
N1 C3 H3A 110.5 . . ?
C4 C3 H3A 110.5 . . ?
N1 C3 H3B 110.5 . . ?
C4 C3 H3B 110.5 . . ?
H3A C3 H3B 108.7 . . ?
O4 C4 O3 124.09(12) . . ?
O4 C4 C3 125.03(11) . . ?
O3 C4 C3 110.87(9) . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C13 C6 C7 112.17(9) . . ?
C13 C6 B1 108.99(9) . . ?
C7 C6 B1 112.07(8) . . ?
C13 C6 H6A 107.8 . . ?
C7 C6 H6A 107.8 . . ?
B1 C6 H6A 107.8 . . ?
C8 C7 C12 110.45(9) . . ?
C8 C7 C6 110.70(9) . . ?
C12 C7 C6 114.36(9) . . ?
C8 C7 H7A 107.0 . . ?
C12 C7 H7A 107.0 . . ?
C6 C7 H7A 107.0 . . ?
C9 C8 C7 112.00(9) . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 110.54(10) . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C9 111.01(10) . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C12 111.30(10) . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C7 111.56(9) . . ?
C11 C12 H12A 109.3 . . ?
C7 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C7 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
N2 C13 C6 121.29(10) . . ?
N2 C13 H13A 119.4 . . ?
C6 C13 H13A 119.4 . . ?
O3 B1 O1 110.98(9) . . ?
O3 B1 C6 114.01(9) . . ?
O1 B1 C6 113.04(9) . . ?
O3 B1 N1 102.25(8) . . ?
O1 B1 N1 98.61(8) . . ?
C6 B1 N1 116.52(9) . . ?
N1S C1S C2S 179.58(18) . . ?
C1S C2S H2S1 109.5 . . ?
C1S C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
C1S C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -151.17(9) . . . . ?
C3 N1 C1 C2 84.15(11) . . . . ?
B1 N1 C1 C2 -23.95(11) . . . . ?
B1 O1 C2 O2 -169.17(11) . . . . ?
B1 O1 C2 C1 9.21(12) . . . . ?
N1 C1 C2 O2 -170.63(11) . . . . ?
N1 C1 C2 O1 11.01(12) . . . . ?
C1 N1 C3 C4 -133.31(9) . . . . ?
C5 N1 C3 C4 100.47(10) . . . . ?
B1 N1 C3 C4 -23.44(10) . . . . ?
B1 O3 C4 O4 -174.13(11) . . . . ?
B1 O3 C4 C3 4.77(12) . . . . ?
N1 C3 C4 O4 -167.33(11) . . . . ?
N1 C3 C4 O3 13.78(12) . . . . ?
C13 C6 C7 C8 -60.62(12) . . . . ?
B1 C6 C7 C8 176.40(9) . . . . ?
C13 C6 C7 C12 64.90(12) . . . . ?
B1 C6 C7 C12 -58.07(12) . . . . ?
C12 C7 C8 C9 54.88(13) . . . . ?
C6 C7 C8 C9 -177.42(9) . . . . ?
C7 C8 C9 C10 -56.35(13) . . . . ?
C8 C9 C10 C11 56.67(13) . . . . ?
C9 C10 C11 C12 -56.52(14) . . . . ?
C10 C11 C12 C7 55.39(14) . . . . ?
C8 C7 C12 C11 -54.05(13) . . . . ?
C6 C7 C12 C11 -179.71(9) . . . . ?
O5 N2 C13 C6 174.46(9) . . . . ?
C7 C6 C13 N2 134.05(11) . . . . ?
B1 C6 C13 N2 -101.25(12) . . . . ?
C4 O3 B1 O1 85.06(11) . . . . ?
C4 O3 B1 C6 -145.91(9) . . . . ?
C4 O3 B1 N1 -19.26(11) . . . . ?
C2 O1 B1 O3 -129.63(9) . . . . ?
C2 O1 B1 C6 100.83(10) . . . . ?
C2 O1 B1 N1 -22.89(10) . . . . ?
C13 C6 B1 O3 -171.77(9) . . . . ?
C7 C6 B1 O3 -47.01(12) . . . . ?
C13 C6 B1 O1 -43.79(12) . . . . ?
C7 C6 B1 O1 80.97(11) . . . . ?
C13 C6 B1 N1 69.42(11) . . . . ?
C7 C6 B1 N1 -165.82(9) . . . . ?
C1 N1 B1 O3 141.56(8) . . . . ?
C5 N1 B1 O3 -93.64(10) . . . . ?
C3 N1 B1 O3 25.64(10) . . . . ?
C1 N1 B1 O1 27.76(10) . . . . ?
C5 N1 B1 O1 152.57(9) . . . . ?
C3 N1 B1 O1 -88.16(9) . . . . ?
C1 N1 B1 C6 -93.43(10) . . . . ?
C5 N1 B1 C6 31.37(13) . . . . ?
C3 N1 B1 C6 150.64(9) . . . . ?

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
O5 H5O N2 0.96(2) 1.87(2) 2.7790(13) 156.7(17) 3_675

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.033

