# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_OSTriOMeSiB
_database_code_depnum_ccdc_archive 'CCDC 2060900'
loop_
_audit_author_name
_audit_author_address
'Jordi Benet-Buchholz'
;Institute of Chemical Research of Catalonia ICIQ
Spain
;
_audit_update_record             
;
2021-02-03 deposited with the CCDC.	2021-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H33 B O5 Si'
_chemical_formula_weight         392.36

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'
Si Si 0.0817 0.0704 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.32916(12)
_cell_length_b                   16.4248(2)
_cell_length_c                   18.8570(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.2007(16)
_cell_angle_gamma                90
_cell_volume                     2234.12(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14675
_cell_measurement_theta_min      2.6390
_cell_measurement_theta_max      34.3000

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.131
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97216
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_source_power             50
_diffrn_source_current           24
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            27323
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.480
_diffrn_reflns_theta_max         34.428
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8944
_reflns_number_gt                8095
_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 1.171.40.35 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.35 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35 (Rigaku OD, 2018)'

_computing_structure_solution    
;
  SHELXT V2018/2 (Sheldrick 2018); G.M. Sheldrick (2015)
 "SHELXT - Integrated space-group and crystal-structure
 determination", Acta Cryst., A71, 3-8. 
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
 SHELXle: C.B. Huebschle, G.M. Sheldrick & B. Dittrich
 J.Appl.Cryst. (2011) 44, 1281-1284.
;
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0512P)²+0.3852P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8944
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0903
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.002
_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
Si1 Si 0.49432(2) 0.88678(2) 0.11276(2) 0.01436(4) Uani 1 1 d . . . . .
O1 O 0.28688(6) 1.05621(3) 0.13371(2) 0.01502(8) Uani 1 1 d . . . . .
O2 O 0.43463(7) 1.07834(3) 0.24991(2) 0.01509(8) Uani 1 1 d . . . . .
O3 O 0.69911(6) 0.85478(3) 0.38911(2) 0.01621(8) Uani 1 1 d . . . . .
O4 O 0.23171(7) 0.94222(3) 0.52546(2) 0.01802(9) Uani 1 1 d . . . . .
O5 O 0.12443(6) 0.95413(3) 0.26967(2) 0.01772(9) Uani 1 1 d . . . . .
C1 C 0.44663(8) 0.93108(3) 0.19952(3) 0.01250(9) Uani 1 1 d . . . . .
C2 C 0.25193(8) 1.14144(4) 0.14902(3) 0.01455(10) Uani 1 1 d . . . . .
C3 C 0.05456(9) 1.14638(5) 0.16435(4) 0.02288(13) Uani 1 1 d . . . . .
H3A H 0.021976 1.203470 0.170659 0.034 Uiso 1 1 calc R U . . .
H3B H 0.046695 1.115929 0.208401 0.034 Uiso 1 1 calc R U . . .
H3C H -0.031673 1.122927 0.123845 0.034 Uiso 1 1 calc R U . . .
C4 C 0.26772(10) 1.19224(4) 0.08290(4) 0.02121(12) Uani 1 1 d . . . . .
H4A H 0.261507 1.250175 0.094690 0.032 Uiso 1 1 calc R U . . .
H4B H 0.165598 1.178583 0.043727 0.032 Uiso 1 1 calc R U . . .
H4C H 0.386209 1.180699 0.067709 0.032 Uiso 1 1 calc R U . . .
C5 C 0.40440(8) 1.15867(4) 0.21674(3) 0.01435(10) Uani 1 1 d . . . . .
C6 C 0.34749(11) 1.21768(4) 0.27103(4) 0.02272(13) Uani 1 1 d . . . . .
H6A H 0.313419 1.270077 0.247507 0.034 Uiso 1 1 calc R U . . .
H6B H 0.451319 1.225535 0.310986 0.034 Uiso 1 1 calc R U . . .
H6C H 0.241075 1.195463 0.289569 0.034 Uiso 1 1 calc R U . . .
C7 C 0.58987(9) 1.18456(4) 0.19736(4) 0.02146(12) Uani 1 1 d . . . . .
H7A H 0.579929 1.240360 0.178671 0.032 Uiso 1 1 calc R U . . .
H7B H 0.621998 1.147794 0.160526 0.032 Uiso 1 1 calc R U . . .
H7C H 0.686567 1.182115 0.240460 0.032 Uiso 1 1 calc R U . . .
C8 C 0.47212(8) 0.88563(3) 0.26051(3) 0.01269(9) Uani 1 1 d . . . . .
H8 H 0.535174 0.835362 0.258592 0.015 Uiso 1 1 calc R U . . .
C9 C 0.41334(8) 0.90509(3) 0.32964(3) 0.01217(9) Uani 1 1 d . . . . .
C10 C 0.52826(8) 0.88492(3) 0.39520(3) 0.01232(9) Uani 1 1 d . . . . .
C11 C 0.47422(8) 0.89601(4) 0.46219(3) 0.01338(10) Uani 1 1 d . . . . .
H11 H 0.554612 0.881580 0.505596 0.016 Uiso 1 1 calc R U . . .
C12 C 0.29949(8) 0.92877(4) 0.46347(3) 0.01373(10) Uani 1 1 d . . . . .
C13 C 0.17999(8) 0.95026(4) 0.39991(3) 0.01506(10) Uani 1 1 d . . . . .
H13 H 0.061730 0.973063 0.401613 0.018 Uiso 1 1 calc R U . . .
C14 C 0.23700(8) 0.93772(4) 0.33394(3) 0.01352(10) Uani 1 1 d . . . . .
C15 C 0.82384(9) 0.83625(4) 0.45462(3) 0.01902(11) Uani 1 1 d . . . . .
H15A H 0.941430 0.816411 0.443240 0.029 Uiso 1 1 calc R U . . .
H15B H 0.769032 0.794183 0.481158 0.029 Uiso 1 1 calc R U . . .
H15C H 0.846348 0.885473 0.484244 0.029 Uiso 1 1 calc R U . . .
C16 C 0.34499(10) 0.91609(4) 0.59147(3) 0.01930(11) Uani 1 1 d . . . . .
H16A H 0.280630 0.927184 0.631776 0.029 Uiso 1 1 calc R U . . .
H16B H 0.462924 0.945691 0.598718 0.029 Uiso 1 1 calc R U . . .
H16C H 0.368812 0.857535 0.589016 0.029 Uiso 1 1 calc R U . . .
C17 C -0.06507(9) 0.97227(7) 0.27147(4) 0.03118(18) Uani 1 1 d . . . . .
H17A H -0.134524 0.975640 0.222122 0.047 Uiso 1 1 calc R U . . .
H17B H -0.073043 1.024457 0.295933 0.047 Uiso 1 1 calc R U . . .
H17C H -0.117793 0.929182 0.297597 0.047 Uiso 1 1 calc R U . . .
C18 C 0.60297(12) 0.78323(5) 0.12688(4) 0.02611(15) Uani 1 1 d . . . . .
H18A H 0.626063 0.761915 0.080743 0.039 Uiso 1 1 calc R U . . .
H18B H 0.519057 0.746446 0.146489 0.039 Uiso 1 1 calc R U . . .
H18C H 0.720519 0.787252 0.160796 0.039 Uiso 1 1 calc R U . . .
C19 C 0.65730(10) 0.95428(5) 0.07333(4) 0.02244(13) Uani 1 1 d . . . . .
H19A H 0.654041 0.939660 0.022741 0.034 Uiso 1 1 calc R U . . .
H19B H 0.783496 0.947222 0.100258 0.034 Uiso 1 1 calc R U . . .
H19C H 0.619438 1.011212 0.076422 0.034 Uiso 1 1 calc R U . . .
C20 C 0.26683(11) 0.87689(4) 0.04966(4) 0.02238(13) Uani 1 1 d . . . . .
H20A H 0.288668 0.858602 0.002406 0.034 Uiso 1 1 calc R U . . .
H20B H 0.204126 0.929812 0.044642 0.034 Uiso 1 1 calc R U . . .
H20C H 0.188861 0.837081 0.068975 0.034 Uiso 1 1 calc R U . . .
B1 B 0.38088(9) 1.02163(4) 0.19633(3) 0.01283(10) Uani 1 1 d . . . . .


_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
Si1 C20 1.8760(7) . ?
Si1 C18 1.8769(7) . ?
Si1 C19 1.8770(7) . ?
Si1 C1 1.8791(6) . ?
O1 B1 1.3796(8) . ?
O1 C2 1.4610(7) . ?
O2 B1 1.3794(8) . ?
O2 C5 1.4603(7) . ?
O3 C10 1.3701(7) . ?
O3 C15 1.4333(8) . ?
O4 C12 1.3667(7) . ?
O4 C16 1.4342(8) . ?
O5 C14 1.3668(7) . ?
O5 C17 1.4267(8) . ?
C1 C8 1.3559(8) . ?
C1 B1 1.5613(9) . ?
C2 C4 1.5215(9) . ?
C2 C3 1.5267(9) . ?
C2 C5 1.5666(8) . ?
C5 C6 1.5208(9) . ?
C5 C7 1.5291(9) . ?
C8 C9 1.4785(8) . ?
C9 C10 1.4067(8) . ?
C9 C14 1.4146(8) . ?
C10 C11 1.4010(8) . ?
C11 C12 1.3932(8) . ?
C12 C13 1.3987(8) . ?
C13 C14 1.3960(8) . ?

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
C20 Si1 C18 108.58(4) . . ?
C20 Si1 C19 110.88(3) . . ?
C18 Si1 C19 107.92(4) . . ?
C20 Si1 C1 107.72(3) . . ?
C18 Si1 C1 111.53(3) . . ?
C19 Si1 C1 110.22(3) . . ?
B1 O1 C2 107.69(5) . . ?
B1 O2 C5 107.12(5) . . ?
C10 O3 C15 117.22(5) . . ?
C12 O4 C16 116.85(5) . . ?
C14 O5 C17 117.22(5) . . ?
C8 C1 B1 123.53(5) . . ?
C8 C1 Si1 120.42(4) . . ?
B1 C1 Si1 116.04(4) . . ?
O1 C2 C4 108.79(5) . . ?
O1 C2 C3 107.07(5) . . ?
C4 C2 C3 109.76(5) . . ?
O1 C2 C5 102.09(4) . . ?
C4 C2 C5 114.96(5) . . ?
C3 C2 C5 113.52(5) . . ?
O2 C5 C6 109.05(5) . . ?
O2 C5 C7 106.25(5) . . ?
C6 C5 C7 110.18(5) . . ?
O2 C5 C2 102.60(4) . . ?
C6 C5 C2 115.01(5) . . ?
C7 C5 C2 113.05(5) . . ?
C1 C8 C9 127.66(5) . . ?
C10 C9 C14 116.73(5) . . ?
C10 C9 C8 120.09(5) . . ?
C14 C9 C8 122.97(5) . . ?
O3 C10 C11 122.08(5) . . ?
O3 C10 C9 115.17(5) . . ?
C11 C10 C9 122.75(5) . . ?
C12 C11 C10 118.25(5) . . ?
O4 C12 C11 123.49(5) . . ?
O4 C12 C13 115.14(5) . . ?
C11 C12 C13 121.38(5) . . ?
C14 C13 C12 119.05(5) . . ?
O5 C14 C13 122.15(5) . . ?
O5 C14 C9 115.98(5) . . ?
C13 C14 C9 121.85(5) . . ?
O2 B1 O1 112.55(5) . . ?
O2 B1 C1 124.66(5) . . ?
O1 B1 C1 121.95(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
C20 Si1 C1 C8 112.14(5) . . . . ?
C18 Si1 C1 C8 -6.91(6) . . . . ?
C19 Si1 C1 C8 -126.77(5) . . . . ?
C20 Si1 C1 B1 -68.83(5) . . . . ?
C18 Si1 C1 B1 172.12(5) . . . . ?
C19 Si1 C1 B1 52.27(5) . . . . ?
B1 O1 C2 C4 144.07(5) . . . . ?
B1 O1 C2 C3 -97.37(6) . . . . ?
B1 O1 C2 C5 22.14(6) . . . . ?
B1 O2 C5 C6 146.19(5) . . . . ?
B1 O2 C5 C7 -95.07(6) . . . . ?
B1 O2 C5 C2 23.81(6) . . . . ?
O1 C2 C5 O2 -27.64(5) . . . . ?
C4 C2 C5 O2 -145.23(5) . . . . ?
C3 C2 C5 O2 87.24(6) . . . . ?
O1 C2 C5 C6 -145.89(5) . . . . ?
C4 C2 C5 C6 96.52(7) . . . . ?
C3 C2 C5 C6 -31.02(8) . . . . ?
O1 C2 C5 C7 86.36(6) . . . . ?
C4 C2 C5 C7 -31.23(7) . . . . ?
C3 C2 C5 C7 -158.77(6) . . . . ?
B1 C1 C8 C9 12.02(10) . . . . ?
Si1 C1 C8 C9 -169.02(5) . . . . ?
C1 C8 C9 C10 -142.01(6) . . . . ?
C1 C8 C9 C14 43.41(9) . . . . ?
C15 O3 C10 C11 -1.23(8) . . . . ?
C15 O3 C10 C9 177.70(5) . . . . ?
C14 C9 C10 O3 -178.94(5) . . . . ?
C8 C9 C10 O3 6.15(8) . . . . ?
C14 C9 C10 C11 -0.03(8) . . . . ?
C8 C9 C10 C11 -174.94(5) . . . . ?
O3 C10 C11 C12 178.54(5) . . . . ?
C9 C10 C11 C12 -0.30(9) . . . . ?
C16 O4 C12 C11 -3.87(9) . . . . ?
C16 O4 C12 C13 176.05(5) . . . . ?
C10 C11 C12 O4 179.89(5) . . . . ?
C10 C11 C12 C13 -0.02(9) . . . . ?
O4 C12 C13 C14 -179.25(5) . . . . ?
C11 C12 C13 C14 0.66(9) . . . . ?
C17 O5 C14 C13 -9.89(10) . . . . ?
C17 O5 C14 C9 168.44(7) . . . . ?
C12 C13 C14 O5 177.22(6) . . . . ?
C12 C13 C14 C9 -1.02(9) . . . . ?
C10 C9 C14 O5 -177.64(5) . . . . ?
C8 C9 C14 O5 -2.89(8) . . . . ?
C10 C9 C14 C13 0.70(9) . . . . ?
C8 C9 C14 C13 175.45(6) . . . . ?
C5 O2 B1 O1 -10.99(7) . . . . ?
C5 O2 B1 C1 158.68(5) . . . . ?
C2 O1 B1 O2 -8.22(7) . . . . ?
C2 O1 B1 C1 -178.21(5) . . . . ?
C8 C1 B1 O2 37.72(9) . . . . ?
Si1 C1 B1 O2 -141.28(5) . . . . ?
C8 C1 B1 O1 -153.53(6) . . . . ?
Si1 C1 B1 O1 27.47(7) . . . . ?

_refine_diff_density_max         0.584
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.046



