# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1961105'
loop_
_audit_author_name
_audit_author_address
'Andrew White'
;Imperial College London
United Kingdom
;
_audit_update_record             
;
2019-10-24 deposited with the CCDC.	2020-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H19 B N2 O5'
_chemical_formula_sum            'C20 H19 B N2 O5'
_chemical_formula_weight         378.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_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                   9.8085(5)
_cell_length_b                   8.9262(4)
_cell_length_c                   21.7277(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.222(5)
_cell_angle_gamma                90
_cell_volume                     1877.72(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1537
_cell_measurement_theta_min      3.1100
_cell_measurement_theta_max      28.0550

_exptl_crystal_description       'blocky needles'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.756
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.125
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_reflns_number            6389
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.471
_diffrn_reflns_theta_max         28.211
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.805
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.805
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.805
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             3720
_reflns_number_gt                2805
_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       'CrysAlisPro, Rigaku OD'
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_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)+(0.0386P)²+0.2745P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0068(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3720
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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_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
N1 N 0.46653(12) 0.13475(14) 0.35158(5) 0.0205(3) Uani 1 1 d . . . . .
C2 C 0.39866(17) 0.05969(17) 0.40031(7) 0.0258(4) Uani 1 1 d . . . . .
H2A H 0.300760 0.037238 0.383843 0.031 Uiso 1 1 calc R U . . .
H2B H 0.402398 0.124843 0.437418 0.031 Uiso 1 1 calc R U . . .
C3 C 0.47816(17) -0.08289(18) 0.41696(8) 0.0280(4) Uani 1 1 d . . . . .
O3 O 0.47295(13) -0.15733(13) 0.46266(5) 0.0363(3) Uani 1 1 d . . . . .
O4 O 0.55534(12) -0.11741(12) 0.37370(5) 0.0311(3) Uani 1 1 d . . . . .
C5 C 0.36464(16) 0.18790(18) 0.29769(7) 0.0251(4) Uani 1 1 d . . . . .
H5A H 0.402487 0.273229 0.276700 0.030 Uiso 1 1 calc R U . . .
H5B H 0.277892 0.220003 0.311607 0.030 Uiso 1 1 calc R U . . .
C6 C 0.33905(17) 0.0549(2) 0.25422(7) 0.0284(4) Uani 1 1 d . . . . .
O6 O 0.24920(12) 0.04753(15) 0.20963(5) 0.0419(3) Uani 1 1 d . . . . .
O7 O 0.43154(11) -0.05206(12) 0.27100(5) 0.0302(3) Uani 1 1 d . . . . .
B8 B 0.54313(19) -0.0092(2) 0.32260(8) 0.0244(4) Uani 1 1 d . . . . .
C9 C 0.56561(15) 0.25427(17) 0.37892(7) 0.0225(3) Uani 1 1 d . . . . .
H9A H 0.619750 0.287744 0.346713 0.027 Uiso 1 1 calc R U . . .
H9B H 0.631038 0.210541 0.413710 0.027 Uiso 1 1 calc R U . . .
C10 C 0.49655(16) 0.38991(17) 0.40297(7) 0.0254(4) Uani 1 1 d . . . . .
H10A H 0.429431 0.433156 0.368684 0.031 Uiso 1 1 calc R U . . .
H10B H 0.445153 0.358094 0.436408 0.031 Uiso 1 1 calc R U . . .
C11 C 0.60095(16) 0.50772(18) 0.42804(7) 0.0267(4) Uani 1 1 d . . . . .
H11A H 0.652156 0.542301 0.394952 0.032 Uiso 1 1 calc R U . . .
H11B H 0.554461 0.594963 0.443709 0.032 Uiso 1 1 calc R U . . .
O12 O 0.69340(11) 0.43844(12) 0.47788(5) 0.0284(3) Uani 1 1 d . . . . .
C13 C 0.79268(16) 0.52345(18) 0.51190(7) 0.0261(4) Uani 1 1 d . . . . .
C14 C 0.88522(17) 0.4458(2) 0.55630(7) 0.0292(4) Uani 1 1 d . . . . .
C15 C 0.98892(18) 0.5222(2) 0.59484(8) 0.0407(5) Uani 1 1 d . . . . .
H15A H 1.051878 0.468848 0.624778 0.049 Uiso 1 1 calc R U . . .
C16 C 1.0005(2) 0.6755(2) 0.58965(9) 0.0461(5) Uani 1 1 d . . . . .
H16A H 1.070624 0.728259 0.616341 0.055 Uiso 1 1 calc R U . . .
C17 C 0.91005(19) 0.7517(2) 0.54559(9) 0.0423(5) Uani 1 1 d . . . . .
H17A H 0.918792 0.857201 0.542083 0.051 Uiso 1 1 calc R U . . .
C18 C 0.80624(17) 0.67763(19) 0.50616(8) 0.0326(4) Uani 1 1 d . . . . .
H18A H 0.745273 0.731632 0.475641 0.039 Uiso 1 1 calc R U . . .
C19 C 0.87209(18) 0.2857(2) 0.56145(8) 0.0344(4) Uani 1 1 d . . . . .
N20 N 0.86304(17) 0.1592(2) 0.56727(8) 0.0509(5) Uani 1 1 d . . . . .
C21 C 0.68394(16) 0.02367(17) 0.29851(7) 0.0246(4) Uani 1 1 d . . . . .
C22 C 0.68559(18) 0.10686(19) 0.24432(8) 0.0319(4) Uani 1 1 d . . . . .
H22A H 0.600940 0.144106 0.222228 0.038 Uiso 1 1 calc R U . . .
C23 C 0.8069(2) 0.1367(2) 0.22179(9) 0.0441(5) Uani 1 1 d . . . . .
H23A H 0.805197 0.195834 0.185315 0.053 Uiso 1 1 calc R U . . .
C24 C 0.9298(2) 0.0806(3) 0.25232(9) 0.0510(6) Uani 1 1 d . . . . .
H24A H 1.013273 0.099953 0.236808 0.061 Uiso 1 1 calc R U . . .
C25 C 0.93145(19) -0.0033(3) 0.30525(9) 0.0480(5) Uani 1 1 d . . . . .
H25A H 1.016281 -0.042944 0.326133 0.058 Uiso 1 1 calc R U . . .
C26 C 0.81015(17) -0.0308(2) 0.32856(8) 0.0359(4) Uani 1 1 d . . . . .
H26A H 0.813327 -0.087899 0.365670 0.043 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
N1 C5 1.4899(18) . ?
N1 C2 1.4964(19) . ?
N1 C9 1.5001(19) . ?
N1 B8 1.662(2) . ?
C2 C3 1.506(2) . ?
C3 O3 1.2027(19) . ?
C3 O4 1.334(2) . ?
O4 B8 1.462(2) . ?
C5 C6 1.513(2) . ?
C6 O6 1.2025(18) . ?
C6 O7 1.3272(19) . ?
O7 B8 1.486(2) . ?
B8 C21 1.581(2) . ?
C9 C10 1.520(2) . ?
C10 C11 1.508(2) . ?
C11 O12 1.4361(18) . ?
O12 C13 1.3564(18) . ?
C13 C18 1.390(2) . ?
C13 C14 1.398(2) . ?
C14 C15 1.388(2) . ?
C14 C19 1.441(3) . ?
C15 C16 1.380(3) . ?
C16 C17 1.376(3) . ?
C17 C18 1.389(2) . ?
C19 N20 1.142(2) . ?
C21 C26 1.392(2) . ?
C21 C22 1.394(2) . ?
C22 C23 1.383(2) . ?
C23 C24 1.374(3) . ?
C24 C25 1.370(3) . ?
C25 C26 1.388(3) . ?

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
C5 N1 C2 112.35(12) . . ?
C5 N1 C9 113.28(12) . . ?
C2 N1 C9 111.81(11) . . ?
C5 N1 B8 103.61(11) . . ?
C2 N1 B8 101.62(11) . . ?
C9 N1 B8 113.34(11) . . ?
N1 C2 C3 106.04(13) . . ?
O3 C3 O4 123.93(15) . . ?
O3 C3 C2 125.19(16) . . ?
O4 C3 C2 110.88(13) . . ?
C3 O4 B8 113.31(12) . . ?
N1 C5 C6 105.31(12) . . ?
O6 C6 O7 124.21(16) . . ?
O6 C6 C5 124.95(16) . . ?
O7 C6 C5 110.82(13) . . ?
C6 O7 B8 114.22(12) . . ?
O4 B8 O7 111.31(13) . . ?
O4 B8 C21 113.85(13) . . ?
O7 B8 C21 112.02(13) . . ?
O4 B8 N1 102.13(12) . . ?
O7 B8 N1 99.32(12) . . ?
C21 B8 N1 117.01(13) . . ?
N1 C9 C10 113.98(12) . . ?
C11 C10 C9 111.44(13) . . ?
O12 C11 C10 106.40(12) . . ?
C13 O12 C11 118.78(12) . . ?
O12 C13 C18 125.14(15) . . ?
O12 C13 C14 115.40(14) . . ?
C18 C13 C14 119.46(15) . . ?
C15 C14 C13 120.32(16) . . ?
C15 C14 C19 120.40(16) . . ?
C13 C14 C19 119.28(14) . . ?
C16 C15 C14 120.00(17) . . ?
C17 C16 C15 119.62(17) . . ?
C16 C17 C18 121.44(18) . . ?
C17 C18 C13 119.15(17) . . ?
N20 C19 C14 178.1(2) . . ?
C26 C21 C22 116.91(16) . . ?
C26 C21 B8 122.58(15) . . ?
C22 C21 B8 120.49(14) . . ?
C23 C22 C21 121.91(17) . . ?
C24 C23 C22 119.79(18) . . ?
C25 C24 C23 119.73(18) . . ?
C24 C25 C26 120.50(18) . . ?
C25 C26 C21 121.14(17) . . ?

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.041

