# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_szn_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1971971'
loop_
_audit_author_name
_audit_author_address
'Bruker APE'
;Jiangsu Ocean university
China
;
_audit_update_record             
;
2019-12-14 deposited with the CCDC.	2020-05-26 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            'C21 H25 B F N O3'
_chemical_formula_weight         369.23

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'
F F 0.0171 0.0103 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.782(4)
_cell_length_b                   9.955(6)
_cell_length_c                   15.273(10)
_cell_angle_alpha                96.852(8)
_cell_angle_beta                 91.313(8)
_cell_angle_gamma                97.621(8)
_cell_volume                     1014.0(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(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    1.209
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.085
_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      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9578
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.080
_diffrn_reflns_theta_max         27.607
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4617
_reflns_number_gt                2299
_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       ?
_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)+(0.1000P)²] 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         4617
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1181
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.2017
_refine_ls_wR_factor_gt          0.1635
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_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
F1 F -0.1297(3) 0.73673(19) 0.98485(12) 0.1244(7) Uani 1 1 d . . . . .
H1A H -0.050(4) 0.284(2) 0.7086(15) 0.069(7) Uiso 1 1 d . . . . .
O1 O 0.3816(2) 0.3965(2) 0.71623(12) 0.0884(6) Uani 1 1 d . . . . .
O2 O 0.3841(2) 0.04245(17) 0.73849(10) 0.0649(5) Uani 1 1 d . . . . .
O3 O 0.7023(2) 0.11066(15) 0.70640(9) 0.0563(4) Uani 1 1 d . . . . .
N1 N 0.0531(3) 0.33768(19) 0.72947(12) 0.0545(5) Uani 1 1 d . . . . .
C1 C 0.2186(3) 0.2089(2) 0.61541(13) 0.0502(5) Uani 1 1 d . . . . .
H1 H 0.129986 0.129803 0.630655 0.060 Uiso 1 1 calc R U . . .
C2 C 0.4252(3) 0.1665(2) 0.60246(14) 0.0565(6) Uani 1 1 d . . . . .
H2A H 0.516689 0.245304 0.590898 0.068 Uiso 1 1 calc R U . . .
H2B H 0.419460 0.098457 0.551084 0.068 Uiso 1 1 calc R U . . .
C3 C 0.2275(3) 0.3225(2) 0.69273(14) 0.0528(5) Uani 1 1 d . . . . .
C4 C 0.0131(3) 0.4398(2) 0.79689(13) 0.0498(5) Uani 1 1 d . . . . .
C5 C -0.1774(3) 0.4713(2) 0.80098(16) 0.0608(6) Uani 1 1 d . . . . .
H5 H -0.274447 0.425155 0.760231 0.073 Uiso 1 1 calc R U . . .
C6 C -0.2277(4) 0.5700(3) 0.86421(18) 0.0741(7) Uani 1 1 d . . . . .
H6 H -0.357227 0.590822 0.866826 0.089 Uiso 1 1 calc R U . . .
C7 C -0.0832(5) 0.6360(3) 0.92259(18) 0.0773(8) Uani 1 1 d . . . . .
C8 C 0.1058(4) 0.6072(3) 0.92200(17) 0.0776(8) Uani 1 1 d . . . . .
H8 H 0.200858 0.653976 0.963458 0.093 Uiso 1 1 calc R U . . .
C9 C 0.1563(4) 0.5068(3) 0.85870(15) 0.0660(7) Uani 1 1 d . . . . .
H9 H 0.285361 0.484721 0.857829 0.079 Uiso 1 1 calc R U . . .
C10 C 0.1275(3) 0.2563(2) 0.53422(13) 0.0506(5) Uani 1 1 d . . . . .
C11 C 0.2253(4) 0.3607(2) 0.49350(16) 0.0708(7) Uani 1 1 d . . . . .
H11 H 0.351023 0.401730 0.515043 0.085 Uiso 1 1 calc R U . . .
C12 C 0.1401(5) 0.4053(3) 0.42125(18) 0.0830(8) Uani 1 1 d . . . . .
H12 H 0.208489 0.475668 0.394387 0.100 Uiso 1 1 calc R U . . .
C13 C -0.0450(5) 0.3462(3) 0.38924(17) 0.0827(8) Uani 1 1 d . . . . .
H13 H -0.103349 0.376458 0.340852 0.099 Uiso 1 1 calc R U . . .
C14 C -0.1438(4) 0.2423(3) 0.42874(18) 0.0818(8) Uani 1 1 d . . . . .
H14 H -0.269534 0.201584 0.406966 0.098 Uiso 1 1 calc R U . . .
C15 C -0.0580(3) 0.1972(3) 0.50090(15) 0.0641(6) Uani 1 1 d . . . . .
H15 H -0.126418 0.126186 0.527157 0.077 Uiso 1 1 calc R U . . .
C16 C 0.7116(3) 0.0155(2) 0.77250(16) 0.0608(6) Uani 1 1 d . . . . .
C17 C 0.5053(3) 0.0142(3) 0.81235(16) 0.0647(6) Uani 1 1 d . . . . .
C18 C 0.4989(5) 0.1312(3) 0.88534(18) 0.0982(10) Uani 1 1 d . . . . .
H18A H 0.555711 0.215264 0.865462 0.147 Uiso 1 1 calc R U . . .
H18B H 0.573817 0.115471 0.936362 0.147 Uiso 1 1 calc R U . . .
H18C H 0.363331 0.136740 0.900326 0.147 Uiso 1 1 calc R U . . .
C19 C 0.4162(4) -0.1180(3) 0.8423(2) 0.0985(10) Uani 1 1 d . . . . .
H19A H 0.396989 -0.187956 0.792715 0.148 Uiso 1 1 calc R U . . .
H19B H 0.290278 -0.107082 0.867745 0.148 Uiso 1 1 calc R U . . .
H19C H 0.504307 -0.143444 0.885642 0.148 Uiso 1 1 calc R U . . .
C20 C 0.8855(4) 0.0650(4) 0.8354(2) 0.1027(11) Uani 1 1 d . . . . .
H20A H 1.006793 0.062854 0.804436 0.154 Uiso 1 1 calc R U . . .
H20B H 0.884439 0.007020 0.881399 0.154 Uiso 1 1 calc R U . . .
H20C H 0.876817 0.156876 0.860885 0.154 Uiso 1 1 calc R U . . .
C21 C 0.7392(6) -0.1211(3) 0.7201(2) 0.1136(12) Uani 1 1 d . . . . .
H21A H 0.620722 -0.156304 0.684634 0.170 Uiso 1 1 calc R U . . .
H21B H 0.764154 -0.184831 0.760160 0.170 Uiso 1 1 calc R U . . .
H21C H 0.850000 -0.108021 0.682575 0.170 Uiso 1 1 calc R U . . .
B1 B 0.5070(4) 0.1073(2) 0.68328(16) 0.0494(6) 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
F1 C7 1.371(3) . ?
O1 C3 1.216(2) . ?
O2 B1 1.357(3) . ?
O2 C17 1.457(3) . ?
O3 B1 1.358(3) . ?
O3 C16 1.470(3) . ?
N1 C3 1.340(3) . ?
N1 C4 1.415(3) . ?
N1 H1A 0.85(2) . ?
C1 C10 1.524(3) . ?
C1 C2 1.526(3) . ?
C1 C3 1.529(3) . ?
C1 H1 0.9800 . ?
C2 B1 1.552(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 C5 1.370(3) . ?
C4 C9 1.384(3) . ?
C5 C6 1.375(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.355(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.350(4) . ?
C8 C9 1.388(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C15 1.375(3) . ?
C10 C11 1.377(3) . ?
C11 C12 1.381(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.367(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.366(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C20 1.496(4) . ?
C16 C21 1.530(4) . ?
C16 C17 1.538(3) . ?
C17 C19 1.500(4) . ?
C17 C18 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 . ?

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
B1 O2 C17 107.92(17) . . ?
B1 O3 C16 106.88(17) . . ?
C3 N1 C4 127.78(19) . . ?
C3 N1 H1A 118.1(17) . . ?
C4 N1 H1A 114.0(17) . . ?
C10 C1 C2 114.27(17) . . ?
C10 C1 C3 109.04(17) . . ?
C2 C1 C3 109.66(17) . . ?
C10 C1 H1 107.9 . . ?
C2 C1 H1 107.9 . . ?
C3 C1 H1 107.9 . . ?
C1 C2 B1 113.22(18) . . ?
C1 C2 H2A 108.9 . . ?
B1 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
B1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
O1 C3 N1 123.1(2) . . ?
O1 C3 C1 121.7(2) . . ?
N1 C3 C1 115.21(18) . . ?
C5 C4 C9 119.2(2) . . ?
C5 C4 N1 117.78(19) . . ?
C9 C4 N1 123.0(2) . . ?
C4 C5 C6 121.2(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 118.2(2) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C8 C7 C6 122.8(2) . . ?
C8 C7 F1 118.3(3) . . ?
C6 C7 F1 118.9(3) . . ?
C7 C8 C9 119.1(2) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C4 C9 C8 119.4(2) . . ?
C4 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C15 C10 C11 118.2(2) . . ?
C15 C10 C1 120.4(2) . . ?
C11 C10 C1 121.4(2) . . ?
C10 C11 C12 121.1(3) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 119.6(2) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 120.7(2) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
O3 C16 C20 109.7(2) . . ?
O3 C16 C21 105.4(2) . . ?
C20 C16 C21 110.4(2) . . ?
O3 C16 C17 101.83(16) . . ?
C20 C16 C17 115.7(2) . . ?
C21 C16 C17 112.9(2) . . ?
O2 C17 C19 109.0(2) . . ?
O2 C17 C18 106.5(2) . . ?
C19 C17 C18 110.1(2) . . ?
O2 C17 C16 101.95(18) . . ?
C19 C17 C16 116.1(2) . . ?
C18 C17 C16 112.5(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2 B1 O3 112.5(2) . . ?
O2 B1 C2 121.8(2) . . ?
O3 B1 C2 125.7(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
C10 C1 C2 B1 -175.14(18) . . . . ?
C3 C1 C2 B1 62.1(2) . . . . ?
C4 N1 C3 O1 2.5(4) . . . . ?
C4 N1 C3 C1 -174.79(18) . . . . ?
C10 C1 C3 O1 -101.9(2) . . . . ?
C2 C1 C3 O1 23.9(3) . . . . ?
C10 C1 C3 N1 75.4(2) . . . . ?
C2 C1 C3 N1 -158.84(19) . . . . ?
C3 N1 C4 C5 154.4(2) . . . . ?
C3 N1 C4 C9 -26.5(3) . . . . ?
C9 C4 C5 C6 1.3(4) . . . . ?
N1 C4 C5 C6 -179.6(2) . . . . ?
C4 C5 C6 C7 0.2(4) . . . . ?
C5 C6 C7 C8 -1.2(4) . . . . ?
C5 C6 C7 F1 178.6(2) . . . . ?
C6 C7 C8 C9 0.6(4) . . . . ?
F1 C7 C8 C9 -179.1(2) . . . . ?
C5 C4 C9 C8 -1.8(4) . . . . ?
N1 C4 C9 C8 179.1(2) . . . . ?
C7 C8 C9 C4 0.9(4) . . . . ?
C2 C1 C10 C15 125.9(2) . . . . ?
C3 C1 C10 C15 -111.1(2) . . . . ?
C2 C1 C10 C11 -55.6(3) . . . . ?
C3 C1 C10 C11 67.5(3) . . . . ?
C15 C10 C11 C12 0.1(4) . . . . ?
C1 C10 C11 C12 -178.4(2) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C11 C12 C13 C14 -0.5(4) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
C11 C10 C15 C14 -0.4(3) . . . . ?
C1 C10 C15 C14 178.2(2) . . . . ?
C13 C14 C15 C10 0.2(4) . . . . ?
B1 O3 C16 C20 -148.7(2) . . . . ?
B1 O3 C16 C21 92.4(2) . . . . ?
B1 O3 C16 C17 -25.6(2) . . . . ?
B1 O2 C17 C19 -146.4(2) . . . . ?
B1 O2 C17 C18 94.9(2) . . . . ?
B1 O2 C17 C16 -23.2(2) . . . . ?
O3 C16 C17 O2 28.9(2) . . . . ?
C20 C16 C17 O2 147.9(2) . . . . ?
C21 C16 C17 O2 -83.6(2) . . . . ?
O3 C16 C17 C19 147.2(2) . . . . ?
C20 C16 C17 C19 -93.9(3) . . . . ?
C21 C16 C17 C19 34.7(3) . . . . ?
O3 C16 C17 C18 -84.7(2) . . . . ?
C20 C16 C17 C18 34.2(3) . . . . ?
C21 C16 C17 C18 162.8(2) . . . . ?
C17 O2 B1 O3 7.8(2) . . . . ?
C17 O2 B1 C2 -173.4(2) . . . . ?
C16 O3 B1 O2 12.3(2) . . . . ?
C16 O3 B1 C2 -166.5(2) . . . . ?
C1 C2 B1 O2 28.5(3) . . . . ?
C1 C2 B1 O3 -152.8(2) . . . . ?

_refine_diff_density_max         0.233
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.046



