# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_A
_database_code_depnum_ccdc_archive 'CCDC 2053886'
loop_
_audit_author_name
_audit_author_address
chenjiangfei
;hunnan
China
;
_audit_update_record             
;
2021-01-17 deposited with the CCDC.	2021-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C17H23BClNO3
_chemical_formula_sum            'C17 H23 B Cl N O3'
_chemical_formula_weight         335.62

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'
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'
Cl Cl 0.1484 0.1585 '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'

_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                   13.213(3)
_cell_length_b                   10.603(2)
_cell_length_c                   14.382(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.903(3)
_cell_angle_gamma                90
_cell_volume                     1827.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2940
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      21.36

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   0.7325
_exptl_transmission_factor_max   1.0000
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.221
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13771
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.565
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3395
_reflns_number_gt                2363
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0926P)²+1.2623P] 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         3395
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.1915
_refine_ls_wR_factor_gt          0.1714
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
B1 B 0.7182(3) 0.4317(3) 0.6644(3) 0.0470(8) Uani 1 1 d . . . . .
C1 C 0.7004(2) 0.8936(3) 0.6127(2) 0.0499(7) Uani 1 1 d . . . . .
C2 C 0.6141(3) 0.8283(3) 0.5388(2) 0.0554(8) Uani 1 1 d . . . . .
H2 H 0.5431 0.8636 0.5090 0.067 Uiso 1 1 calc R U . . .
C3 C 0.6331(2) 0.7096(3) 0.5088(2) 0.0528(8) Uani 1 1 d . . . . .
H3 H 0.5751 0.6644 0.4592 0.063 Uiso 1 1 calc R U . . .
C4 C 0.7387(2) 0.6595(3) 0.5533(2) 0.0443(7) Uani 1 1 d . . . . .
C5 C 0.8238(2) 0.7268(3) 0.6291(2) 0.0431(7) Uani 1 1 d . . . . .
C6 C 0.8077(2) 0.8446(3) 0.6612(2) 0.0465(7) Uani 1 1 d . . . . .
H6 H 0.8652 0.8887 0.7122 0.056 Uiso 1 1 calc R U . . .
C7 C 1.0250(3) 0.6918(3) 0.7512(3) 0.0732(11) Uani 1 1 d . . . . .
H7A H 1.0857 0.6418 0.7514 0.110 Uiso 1 1 calc R U . . .
H7B H 1.0162 0.6769 0.8132 0.110 Uiso 1 1 calc R U . . .
H7C H 1.0406 0.7795 0.7468 0.110 Uiso 1 1 calc R U . . .
C8 C 0.9063(3) 0.5430(3) 0.6163(2) 0.0496(7) Uani 1 1 d . . . . .
C9 C 0.7847(3) 0.5357(3) 0.5366(2) 0.0486(7) Uani 1 1 d . . . . .
C10 C 0.7842(3) 0.5260(4) 0.4299(3) 0.0702(10) Uani 1 1 d . . . . .
H10A H 0.8228 0.5971 0.4188 0.105 Uiso 1 1 calc R U . . .
H10B H 0.7085 0.5252 0.3786 0.105 Uiso 1 1 calc R U . . .
H10C H 0.8209 0.4496 0.4254 0.105 Uiso 1 1 calc R U . . .
C11 C 0.7273(3) 0.4207(3) 0.5597(2) 0.0567(8) Uani 1 1 d . . . . .
H11A H 0.7691 0.3452 0.5604 0.068 Uiso 1 1 calc R U . . .
H11B H 0.6530 0.4117 0.5051 0.068 Uiso 1 1 calc R U . . .
C12 C 0.7693(3) 0.4712(4) 0.8342(3) 0.0670(10) Uani 1 1 d . . . . .
C13 C 0.6448(3) 0.4497(4) 0.7802(3) 0.0671(10) Uani 1 1 d . . . . .
C14 C 0.8160(5) 0.5794(7) 0.9000(4) 0.139(3) Uani 1 1 d . . . . .
H14A H 0.7849 0.6553 0.8625 0.208 Uiso 1 1 calc R U . . .
H14B H 0.8955 0.5801 0.9228 0.208 Uiso 1 1 calc R U . . .
H14C H 0.7985 0.5744 0.9582 0.208 Uiso 1 1 calc R U . . .
C15 C 0.8287(5) 0.3516(7) 0.8986(4) 0.143(3) Uani 1 1 d . . . . .
H15A H 0.9037 0.3470 0.9044 0.214 Uiso 1 1 calc R U . . .
H15B H 0.7885 0.2772 0.8649 0.214 Uiso 1 1 calc R U . . .
H15C H 0.8301 0.3575 0.9657 0.214 Uiso 1 1 calc R U . . .
C16 C 0.5885(6) 0.3716(8) 0.8265(5) 0.168(3) Uani 1 1 d . . . . .
H16A H 0.6107 0.2853 0.8269 0.252 Uiso 1 1 calc R U . . .
H16B H 0.5093 0.3786 0.7876 0.252 Uiso 1 1 calc R U . . .
H16C H 0.6083 0.3990 0.8956 0.252 Uiso 1 1 calc R U . . .
C17 C 0.5857(5) 0.5823(7) 0.7578(4) 0.146(3) Uani 1 1 d . . . . .
H17A H 0.5187 0.5782 0.6955 0.220 Uiso 1 1 calc R U . . .
H17B H 0.6350 0.6444 0.7509 0.220 Uiso 1 1 calc R U . . .
H17C H 0.5674 0.6053 0.8135 0.220 Uiso 1 1 calc R U . . .
Cl1 Cl 0.67599(7) 1.04502(9) 0.64711(7) 0.0697(3) Uani 1 1 d . . . . .
N1 N 0.92322(19) 0.6575(2) 0.66386(19) 0.0478(6) Uani 1 1 d . . . . .
O1 O 0.9774(2) 0.4625(2) 0.6341(2) 0.0655(7) Uani 1 1 d . . . . .
O2 O 0.80408(18) 0.4727(2) 0.75062(16) 0.0587(6) Uani 1 1 d . . . . .
O3 O 0.62571(19) 0.4055(3) 0.67845(17) 0.0665(7) 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
B1 O3 1.349(4) . ?
B1 O2 1.352(4) . ?
B1 C11 1.565(5) . ?
C1 C2 1.374(4) . ?
C1 C6 1.390(4) . ?
C1 Cl1 1.749(3) . ?
C2 C3 1.388(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(4) . ?
C4 C9 1.507(4) . ?
C5 C6 1.379(4) . ?
C5 N1 1.401(3) . ?
C6 H6 0.9300 . ?
C7 N1 1.448(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 O1 1.214(4) . ?
C8 N1 1.365(4) . ?
C8 C9 1.533(4) . ?
C9 C10 1.536(4) . ?
C9 C11 1.545(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C14 1.449(6) . ?
C12 O2 1.457(4) . ?
C12 C13 1.512(5) . ?
C12 C15 1.571(7) . ?
C13 C16 1.448(6) . ?
C13 O3 1.454(4) . ?
C13 C17 1.575(7) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
O3 B1 O2 113.1(3) . . ?
O3 B1 C11 124.8(3) . . ?
O2 B1 C11 122.1(3) . . ?
C2 C1 C6 122.6(3) . . ?
C2 C1 Cl1 119.3(2) . . ?
C6 C1 Cl1 118.1(2) . . ?
C1 C2 C3 119.8(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 C9 131.4(3) . . ?
C5 C4 C9 109.0(2) . . ?
C6 C5 C4 122.7(3) . . ?
C6 C5 N1 127.6(3) . . ?
C4 C5 N1 109.7(3) . . ?
C5 C6 C1 116.1(3) . . ?
C5 C6 H6 122.0 . . ?
C1 C6 H6 122.0 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 N1 124.8(3) . . ?
O1 C8 C9 126.6(3) . . ?
N1 C8 C9 108.6(2) . . ?
C4 C9 C8 101.7(2) . . ?
C4 C9 C10 112.7(3) . . ?
C8 C9 C10 108.3(3) . . ?
C4 C9 C11 112.6(3) . . ?
C8 C9 C11 109.5(3) . . ?
C10 C9 C11 111.5(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 B1 113.1(3) . . ?
C9 C11 H11A 109.0 . . ?
B1 C11 H11A 109.0 . . ?
C9 C11 H11B 109.0 . . ?
B1 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C14 C12 O2 109.6(3) . . ?
C14 C12 C13 121.8(4) . . ?
O2 C12 C13 103.3(3) . . ?
C14 C12 C15 106.6(5) . . ?
O2 C12 C15 104.0(3) . . ?
C13 C12 C15 110.2(4) . . ?
C16 C13 O3 111.9(4) . . ?
C16 C13 C12 120.5(4) . . ?
O3 C13 C12 104.8(3) . . ?
C16 C13 C17 107.4(5) . . ?
O3 C13 C17 102.8(3) . . ?
C12 C13 C17 108.0(4) . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C8 N1 C5 110.9(2) . . ?
C8 N1 C7 123.7(3) . . ?
C5 N1 C7 124.5(3) . . ?
B1 O2 C12 108.6(2) . . ?
B1 O3 C13 107.5(2) . . ?

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
C6 C1 C2 C3 -1.1(5) . . . . ?
Cl1 C1 C2 C3 178.2(2) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C3 C4 C5 1.6(4) . . . . ?
C2 C3 C4 C9 -179.5(3) . . . . ?
C3 C4 C5 C6 -1.2(4) . . . . ?
C9 C4 C5 C6 179.6(3) . . . . ?
C3 C4 C5 N1 179.4(2) . . . . ?
C9 C4 C5 N1 0.2(3) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
N1 C5 C6 C1 179.0(3) . . . . ?
C2 C1 C6 C5 1.5(4) . . . . ?
Cl1 C1 C6 C5 -177.8(2) . . . . ?
C3 C4 C9 C8 -177.3(3) . . . . ?
C5 C4 C9 C8 1.7(3) . . . . ?
C3 C4 C9 C10 66.9(4) . . . . ?
C5 C4 C9 C10 -114.0(3) . . . . ?
C3 C4 C9 C11 -60.2(4) . . . . ?
C5 C4 C9 C11 118.8(3) . . . . ?
O1 C8 C9 C4 178.1(3) . . . . ?
N1 C8 C9 C4 -3.1(3) . . . . ?
O1 C8 C9 C10 -62.9(4) . . . . ?
N1 C8 C9 C10 115.8(3) . . . . ?
O1 C8 C9 C11 58.8(4) . . . . ?
N1 C8 C9 C11 -122.5(3) . . . . ?
C4 C9 C11 B1 -47.9(4) . . . . ?
C8 C9 C11 B1 64.5(3) . . . . ?
C10 C9 C11 B1 -175.7(3) . . . . ?
O3 B1 C11 C9 134.4(3) . . . . ?
O2 B1 C11 C9 -43.7(4) . . . . ?
C14 C12 C13 C16 -93.5(6) . . . . ?
O2 C12 C13 C16 143.0(5) . . . . ?
C15 C12 C13 C16 32.4(6) . . . . ?
C14 C12 C13 O3 139.3(4) . . . . ?
O2 C12 C13 O3 15.8(4) . . . . ?
C15 C12 C13 O3 -94.8(4) . . . . ?
C14 C12 C13 C17 30.2(5) . . . . ?
O2 C12 C13 C17 -93.3(4) . . . . ?
C15 C12 C13 C17 156.1(4) . . . . ?
O1 C8 N1 C5 -177.7(3) . . . . ?
C9 C8 N1 C5 3.5(3) . . . . ?
O1 C8 N1 C7 -8.2(5) . . . . ?
C9 C8 N1 C7 173.0(3) . . . . ?
C6 C5 N1 C8 178.2(3) . . . . ?
C4 C5 N1 C8 -2.4(3) . . . . ?
C6 C5 N1 C7 8.8(5) . . . . ?
C4 C5 N1 C7 -171.8(3) . . . . ?
O3 B1 O2 C12 2.0(4) . . . . ?
C11 B1 O2 C12 -179.7(3) . . . . ?
C14 C12 O2 B1 -142.5(4) . . . . ?
C13 C12 O2 B1 -11.3(4) . . . . ?
C15 C12 O2 B1 103.9(4) . . . . ?
O2 B1 O3 C13 8.8(4) . . . . ?
C11 B1 O3 C13 -169.5(3) . . . . ?
C16 C13 O3 B1 -147.5(5) . . . . ?
C12 C13 O3 B1 -15.3(4) . . . . ?
C17 C13 O3 B1 97.5(4) . . . . ?

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
C6 H6 O1 0.93 2.44 3.355(4) 167.9 2_756
C2 H2 Cl1 0.93 2.98 3.874(3) 161.7 3_676

_refine_diff_density_max         0.704
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.049



