# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_dk2_0m
_database_code_depnum_ccdc_archive 'CCDC 1946768'
loop_
_audit_author_name
_audit_author_address
'Shuzhang Xiao'
;China Three Gorges University
China
;
_audit_update_record             
;
2019-08-13 deposited with the CCDC.	2019-10-30 downloaded from the CCDC.
;
_audit_creation_date             2019-07-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H13 B F2 N2 O'
_chemical_formula_sum            'C20 H13 B F2 N2 O'
_chemical_formula_weight         346.13
_chemical_melting_point          ?
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   7.7955(4)
_cell_length_b                   23.1127(10)
_cell_length_c                   9.1369(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.3580(10)
_cell_angle_gamma                90
_cell_volume                     1571.27(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      79.09
_cell_measurement_theta_min      3.83
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.726
_exptl_absorpt_coefficient_mu    0.889
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6336
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       PLATELET
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.384
_exptl_crystal_size_mid          0.309
_exptl_crystal_size_min          0.038
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            22741
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.458
_diffrn_reflns_theta_min         3.825
_diffrn_ambient_temperature      150.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2994
_reflns_number_total             3383
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3383
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0423
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1368
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C20(H20), C10(H10), C11(H11), C5(H5), C13(H13), C18(H18), C19(H19),
 C6(H6), C12(H12), C3(H3), C1(H1), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
F2 F 0.16923(9) 0.65546(3) 0.81579(7) 0.0297(2) Uani 1 1 d . . . . .
F1 F 0.30326(9) 0.72185(3) 0.70068(8) 0.0310(2) Uani 1 1 d . . . . .
O1 O 0.23315(10) 0.63212(3) 0.58805(8) 0.0265(2) Uani 1 1 d . . . . .
N2 N 0.47759(12) 0.63886(4) 0.82870(10) 0.0227(2) Uani 1 1 d . . . . .
N1 N 0.52039(11) 0.58534(4) 0.81722(10) 0.0227(2) Uani 1 1 d . . . . .
C15 C 0.35400(13) 0.45666(4) 0.57956(11) 0.0231(2) Uani 1 1 d . . . . .
C8 C 0.27210(13) 0.57687(4) 0.58597(12) 0.0230(2) Uani 1 1 d . . . . .
C4 C 0.61008(14) 0.67264(4) 0.93673(11) 0.0241(2) Uani 1 1 d . . . . .
C14 C 0.21750(13) 0.48325(4) 0.45150(11) 0.0237(2) Uani 1 1 d . . . . .
C9 C 0.17773(13) 0.54302(4) 0.45485(11) 0.0235(2) Uani 1 1 d . . . . .
C7 C 0.40923(13) 0.55214(4) 0.70653(11) 0.0219(2) Uani 1 1 d . . . . .
C16 C 0.44892(13) 0.49063(4) 0.70560(11) 0.0223(2) Uani 1 1 d . . . . .
C17 C 0.57719(14) 0.46497(4) 0.83109(11) 0.0252(2) Uani 1 1 d . . . . .
H17 H 0.6392 0.4880 0.9167 0.030 Uiso 1 1 calc R . . . .
C20 C 0.39365(15) 0.39697(5) 0.58209(12) 0.0282(2) Uani 1 1 d . . . . .
H20 H 0.3312 0.3734 0.4979 0.034 Uiso 1 1 calc R . . . .
C10 C 0.04446(14) 0.56918(5) 0.33335(12) 0.0281(2) Uani 1 1 d . . . . .
H10 H 0.0194 0.6093 0.3376 0.034 Uiso 1 1 calc R . . . .
C11 C -0.04950(15) 0.53680(5) 0.20860(12) 0.0304(3) Uani 1 1 d . . . . .
H11 H -0.1388 0.5544 0.1264 0.037 Uiso 1 1 calc R . . . .
C5 C 0.79250(15) 0.66093(5) 0.96413(12) 0.0279(2) Uani 1 1 d . . . . .
H5 H 0.8298 0.6302 0.9115 0.033 Uiso 1 1 calc R . . . .
C13 C 0.11772(14) 0.45148(5) 0.32321(12) 0.0277(2) Uani 1 1 d . . . . .
H13 H 0.1399 0.4112 0.3181 0.033 Uiso 1 1 calc R . . . .
C18 C 0.61328(15) 0.40638(5) 0.83026(12) 0.0288(2) Uani 1 1 d . . . . .
H18 H 0.7004 0.3893 0.9149 0.035 Uiso 1 1 calc R . . . .
C19 C 0.52142(16) 0.37223(5) 0.70468(13) 0.0308(3) Uani 1 1 d . . . . .
H19 H 0.5470 0.3321 0.7038 0.037 Uiso 1 1 calc R . . . .
C6 C 0.91931(16) 0.69456(5) 1.06909(14) 0.0338(3) Uani 1 1 d . . . . .
H6 H 1.0438 0.6872 1.0875 0.041 Uiso 1 1 calc R . . . .
C12 C -0.01202(15) 0.47756(5) 0.20423(12) 0.0305(3) Uani 1 1 d . . . . .
H12 H -0.0766 0.4551 0.1184 0.037 Uiso 1 1 calc R . . . .
C3 C 0.55291(15) 0.71788(5) 1.01177(13) 0.0286(2) Uani 1 1 d . . . . .
H3 H 0.4286 0.7262 0.9910 0.034 Uiso 1 1 calc R . . . .
C1 C 0.86379(17) 0.73902(6) 1.14705(14) 0.0361(3) Uani 1 1 d . . . . .
H1 H 0.9503 0.7615 1.2203 0.043 Uiso 1 1 calc R . . . .
C2 C 0.68168(17) 0.75057(5) 1.11776(14) 0.0338(3) Uani 1 1 d . . . . .
H2 H 0.6446 0.7812 1.1708 0.041 Uiso 1 1 calc R . . . .
B1 B 0.28827(15) 0.66455(5) 0.73231(13) 0.0244(3) 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
F2 B1 1.3819(14) . ?
F1 B1 1.3680(13) . ?
O1 C8 1.3139(13) . ?
O1 B1 1.4649(13) . ?
N2 N1 1.2935(12) . ?
N2 C4 1.4290(12) . ?
N2 B1 1.5908(14) . ?
N1 C7 1.3564(13) . ?
C15 C14 1.4616(14) . ?
C15 C16 1.4078(13) . ?
C15 C20 1.4123(14) . ?
C8 C9 1.4362(14) . ?
C8 C7 1.4073(14) . ?
C4 C5 1.3949(15) . ?
C4 C3 1.3944(15) . ?
C14 C9 1.4181(14) . ?
C14 C13 1.4051(14) . ?
C9 C10 1.4104(14) . ?
C7 C16 1.4554(14) . ?
C16 C17 1.4079(13) . ?
C17 H17 0.9500 . ?
C17 C18 1.3835(15) . ?
C20 H20 0.9500 . ?
C20 C19 1.3814(16) . ?
C10 H10 0.9500 . ?
C10 C11 1.3777(16) . ?
C11 H11 0.9500 . ?
C11 C12 1.4030(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3913(15) . ?
C13 H13 0.9500 . ?
C13 C12 1.3827(16) . ?
C18 H18 0.9500 . ?
C18 C19 1.4008(16) . ?
C19 H19 0.9500 . ?
C6 H6 0.9500 . ?
C6 C1 1.3909(18) . ?
C12 H12 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.3914(15) . ?
C1 H1 0.9500 . ?
C1 C2 1.3898(19) . ?
C2 H2 0.9500 . ?

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
C8 O1 B1 120.22(8) . . ?
N1 N2 C4 115.32(8) . . ?
N1 N2 B1 122.08(8) . . ?
C4 N2 B1 122.58(8) . . ?
N2 N1 C7 118.60(8) . . ?
C16 C15 C14 119.98(9) . . ?
C16 C15 C20 118.18(9) . . ?
C20 C15 C14 121.83(9) . . ?
O1 C8 C9 118.59(9) . . ?
O1 C8 C7 120.55(9) . . ?
C7 C8 C9 120.80(9) . . ?
C5 C4 N2 120.39(9) . . ?
C3 C4 N2 118.56(9) . . ?
C3 C4 C5 121.03(10) . . ?
C9 C14 C15 120.27(9) . . ?
C13 C14 C15 122.52(9) . . ?
C13 C14 C9 117.19(9) . . ?
C14 C9 C8 119.20(9) . . ?
C10 C9 C8 119.78(9) . . ?
C10 C9 C14 121.01(9) . . ?
N1 C7 C8 121.39(9) . . ?
N1 C7 C16 117.87(9) . . ?
C8 C7 C16 120.36(9) . . ?
C15 C16 C7 119.26(9) . . ?
C15 C16 C17 120.23(9) . . ?
C17 C16 C7 120.49(9) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.27(9) . . ?
C18 C17 H17 119.9 . . ?
C15 C20 H20 119.4 . . ?
C19 C20 C15 121.27(10) . . ?
C19 C20 H20 119.4 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.21(10) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.34(10) . . ?
C12 C11 H11 120.3 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.47(10) . . ?
C6 C5 H5 120.3 . . ?
C14 C13 H13 119.3 . . ?
C12 C13 C14 121.40(10) . . ?
C12 C13 H13 119.3 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.06(10) . . ?
C19 C18 H18 120.0 . . ?
C20 C19 C18 119.97(10) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 C5 120.01(11) . . ?
C1 C6 H6 120.0 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.85(10) . . ?
C13 C12 H12 119.6 . . ?
C4 C3 H3 120.7 . . ?
C2 C3 C4 118.64(10) . . ?
C2 C3 H3 120.7 . . ?
C6 C1 H1 120.0 . . ?
C2 C1 C6 119.95(11) . . ?
C2 C1 H1 120.0 . . ?
C3 C2 H2 119.6 . . ?
C1 C2 C3 120.88(11) . . ?
C1 C2 H2 119.6 . . ?
F2 B1 O1 110.72(9) . . ?
F2 B1 N2 107.61(8) . . ?
F1 B1 F2 112.19(9) . . ?
F1 B1 O1 109.02(9) . . ?
F1 B1 N2 110.78(9) . . ?
O1 B1 N2 106.37(8) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
