# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_exp_600
_database_code_depnum_ccdc_archive 'CCDC 2120231'
loop_
_audit_author_name
_audit_author_address
'Yuanqi Wu'
;Changchun University of Technology
China
;
_audit_update_record             
;
2021-11-04 deposited with the CCDC.	2022-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H27 B O3'
_chemical_formula_weight         350.24

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'
B B 0.0090 0.0039 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   8.63440(10)
_cell_length_b                   13.5463(2)
_cell_length_c                   16.9157(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1978.53(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.596
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48365
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.181
_diffrn_reflns_theta_max         74.680
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4005
_reflns_number_gt                3963
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.999

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0393P)²+0.7525P] 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-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0112(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1659 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4005
_refine_ls_number_parameters     241
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0887
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.103
_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
O1 O 0.56674(18) 0.12178(10) 0.28125(9) 0.0275(3) Uani 1 1 d . . . . .
O2 O 0.9274(2) 0.30289(11) 0.38367(11) 0.0409(5) Uani 1 1 d . . . . .
O3 O 0.86151(17) 0.46354(11) 0.39346(10) 0.0311(4) Uani 1 1 d . . . . .
C1 C 0.0881(2) 0.32136(15) 0.03490(11) 0.0238(4) Uani 1 1 d . . . . .
H1 H 0.099394 0.255210 0.021340 0.029 Uiso 1 1 calc R U . . .
C2 C -0.0083(2) 0.38172(18) -0.00974(12) 0.0306(5) Uani 1 1 d . . . . .
H2 H -0.061417 0.355590 -0.052739 0.037 Uiso 1 1 calc R U . . .
C3 C -0.0256(2) 0.47991(17) 0.00924(13) 0.0313(5) Uani 1 1 d . . . . .
H3 H -0.089942 0.519962 -0.021014 0.038 Uiso 1 1 calc R U . . .
C4 C 0.0530(2) 0.51911(16) 0.07355(13) 0.0280(4) Uani 1 1 d . . . . .
H4 H 0.041069 0.585357 0.086622 0.034 Uiso 1 1 calc R U . . .
C5 C 0.1500(2) 0.45888(15) 0.11853(12) 0.0226(4) Uani 1 1 d . . . . .
H5 H 0.203126 0.485453 0.161360 0.027 Uiso 1 1 calc R U . . .
C6 C 0.1682(2) 0.35914(14) 0.09992(11) 0.0196(4) Uani 1 1 d . . . . .
C7 C 0.2709(2) 0.29499(14) 0.14820(10) 0.0176(4) Uani 1 1 d . . . . .
C8 C 0.4175(2) 0.32817(14) 0.17220(10) 0.0182(4) Uani 1 1 d . . . . .
H8 H 0.451042 0.391116 0.158471 0.022 Uiso 1 1 calc R U . . .
C9 C 0.5116(2) 0.26697(13) 0.21625(10) 0.0174(4) Uani 1 1 d . . . . .
C10 C 0.4602(2) 0.17384(14) 0.23763(10) 0.0197(4) Uani 1 1 d . . . . .
C11 C 0.3151(2) 0.13926(14) 0.21689(12) 0.0228(4) Uani 1 1 d . . . . .
H11 H 0.280914 0.077257 0.232775 0.027 Uiso 1 1 calc R U . . .
C12 C 0.2225(2) 0.20096(14) 0.17134(11) 0.0198(4) Uani 1 1 d . . . . .
H12 H 0.125168 0.178919 0.155760 0.024 Uiso 1 1 calc R U . . .
C13 C 0.6716(2) 0.28332(14) 0.25047(10) 0.0192(4) Uani 1 1 d . . . . .
C14 C 0.7108(2) 0.17603(15) 0.27571(13) 0.0269(4) Uani 1 1 d . . . . .
H14A H 0.778397 0.145514 0.236967 0.032 Uiso 1 1 calc R U . . .
H14B H 0.763276 0.176071 0.326411 0.032 Uiso 1 1 calc R U . . .
C15 C 0.6625(2) 0.35223(14) 0.32285(11) 0.0200(4) Uani 1 1 d . . . . .
H15A H 0.590852 0.323639 0.360632 0.024 Uiso 1 1 calc R U . . .
H15B H 0.619303 0.414847 0.305878 0.024 Uiso 1 1 calc R U . . .
C16 C 0.9993(2) 0.45179(15) 0.44329(12) 0.0237(4) Uani 1 1 d . U . . .
C17 C 1.0652(3) 0.35285(16) 0.41394(14) 0.0315(5) Uani 1 1 d . U . . .
C18 C 1.1030(3) 0.53959(19) 0.4322(2) 0.0545(8) Uani 1 1 d . U . . .
H18A H 1.125073 0.547900 0.376958 0.082 Uiso 1 1 calc R U . . .
H18B H 1.197972 0.529405 0.460533 0.082 Uiso 1 1 calc R U . . .
H18C H 1.052291 0.597634 0.451940 0.082 Uiso 1 1 calc R U . . .
C19 C 0.9426(3) 0.4511(3) 0.52743(16) 0.0646(10) Uani 1 1 d . U . . .
H19A H 0.880577 0.508732 0.536856 0.097 Uiso 1 1 calc R U . . .
H19B H 1.029619 0.451072 0.562721 0.097 Uiso 1 1 calc R U . . .
H19C H 0.881295 0.393008 0.536365 0.097 Uiso 1 1 calc R U . . .
C20 C 1.1337(5) 0.2899(2) 0.4795(3) 0.0825(15) Uani 1 1 d . U . . .
H20A H 1.055597 0.276446 0.518408 0.124 Uiso 1 1 calc R U . . .
H20B H 1.218187 0.324594 0.503765 0.124 Uiso 1 1 calc R U . . .
H20C H 1.170695 0.228834 0.457717 0.124 Uiso 1 1 calc R U . . .
C21 C 1.1753(3) 0.3645(4) 0.3456(2) 0.0853(15) Uani 1 1 d . U . . .
H21A H 1.202524 0.300551 0.325462 0.128 Uiso 1 1 calc R U . . .
H21B H 1.267109 0.397888 0.363223 0.128 Uiso 1 1 calc R U . . .
H21C H 1.126560 0.402404 0.304667 0.128 Uiso 1 1 calc R U . . .
C22 C 0.7871(2) 0.32231(19) 0.18990(12) 0.0312(5) Uani 1 1 d . . . . .
H22A H 0.787160 0.280039 0.144355 0.047 Uiso 1 1 calc R U . . .
H22B H 0.888786 0.323543 0.212796 0.047 Uiso 1 1 calc R U . . .
H22C H 0.757993 0.387923 0.174407 0.047 Uiso 1 1 calc R U . . .
B1 B 0.8206(2) 0.37317(16) 0.36664(12) 0.0187(4) 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
O1 C10 1.374(2) . ?
O1 C14 1.448(3) . ?
O2 B1 1.356(3) . ?
O2 C17 1.461(3) . ?
O3 B1 1.352(3) . ?
O3 C16 1.466(2) . ?
C1 C2 1.390(3) . ?
C1 C6 1.396(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.377(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.486(3) . ?
C7 C12 1.396(3) . ?
C7 C8 1.403(3) . ?
C8 C9 1.379(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(3) . ?
C9 C13 1.514(3) . ?
C10 C11 1.383(3) . ?
C11 C12 1.390(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C22 1.524(3) . ?
C13 C15 1.542(3) . ?
C13 C14 1.552(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 B1 1.579(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C18 1.501(3) . ?
C16 C19 1.505(3) . ?
C16 C17 1.538(3) . ?
C17 C21 1.505(4) . ?
C17 C20 1.519(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
C10 O1 C14 106.26(14) . . ?
B1 O2 C17 107.62(16) . . ?
B1 O3 C16 107.83(16) . . ?
C2 C1 C6 120.58(19) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C3 C2 C1 120.46(19) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.96(19) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.70(19) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 118.47(18) . . ?
C5 C6 C7 120.61(17) . . ?
C1 C6 C7 120.93(18) . . ?
C12 C7 C8 118.76(17) . . ?
C12 C7 C6 120.58(17) . . ?
C8 C7 C6 120.66(17) . . ?
C9 C8 C7 119.68(17) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 119.98(18) . . ?
C8 C9 C13 131.00(17) . . ?
C10 C9 C13 109.00(16) . . ?
O1 C10 C11 124.68(17) . . ?
O1 C10 C9 113.16(17) . . ?
C11 C10 C9 122.16(17) . . ?
C10 C11 C12 117.28(17) . . ?
C10 C11 H11 121.4 . . ?
C12 C11 H11 121.4 . . ?
C11 C12 C7 122.11(18) . . ?
C11 C12 H12 118.9 . . ?
C7 C12 H12 118.9 . . ?
C9 C13 C22 112.99(15) . . ?
C9 C13 C15 110.23(16) . . ?
C22 C13 C15 110.94(17) . . ?
C9 C13 C14 99.62(15) . . ?
C22 C13 C14 111.51(17) . . ?
C15 C13 C14 111.08(15) . . ?
O1 C14 C13 107.80(16) . . ?
O1 C14 H14A 110.1 . . ?
C13 C14 H14A 110.1 . . ?
O1 C14 H14B 110.1 . . ?
C13 C14 H14B 110.1 . . ?
H14A C14 H14B 108.5 . . ?
C13 C15 B1 115.92(16) . . ?
C13 C15 H15A 108.3 . . ?
B1 C15 H15A 108.3 . . ?
C13 C15 H15B 108.3 . . ?
B1 C15 H15B 108.3 . . ?
H15A C15 H15B 107.4 . . ?
O3 C16 C18 109.02(17) . . ?
O3 C16 C19 106.28(18) . . ?
C18 C16 C19 108.5(2) . . ?
O3 C16 C17 102.07(15) . . ?
C18 C16 C17 115.4(2) . . ?
C19 C16 C17 114.8(2) . . ?
O2 C17 C21 107.08(19) . . ?
O2 C17 C20 108.2(2) . . ?
C21 C17 C20 111.9(3) . . ?
O2 C17 C16 102.45(15) . . ?
C21 C17 C16 113.0(3) . . ?
C20 C17 C16 113.4(2) . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C13 C22 H22A 109.5 . . ?
C13 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C13 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 B1 O2 112.75(17) . . ?
O3 B1 C15 123.07(17) . . ?
O2 B1 C15 124.15(18) . . ?

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.036

