# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2160248'
loop_
_audit_author_name
_audit_author_address
'Miriding Mutailipu'
;Chinese academic of science
China
;
_audit_update_record             
;
2022-03-20 deposited with the CCDC.	2022-04-03 downloaded from the CCDC.
;
_audit_creation_date             2022-02-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'B3 F4 H O4, 2(C3 H7 N6)'
_chemical_formula_sum            'C6 H15 B3 F4 N12 O4'
_chemical_formula_weight         427.73
_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 0.0033 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'
F F 0.0171 0.0103 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9987(4)
_cell_length_b                   10.0087(4)
_cell_length_c                   11.5314(5)
_cell_angle_alpha                90.031(2)
_cell_angle_beta                 94.120(2)
_cell_angle_gamma                94.442(2)
_cell_volume                     803.23(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1285
_cell_measurement_temperature    300.0
_cell_measurement_theta_max      22.128
_cell_measurement_theta_min      2.435
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1362 before and 0.0706 after correction.
The Ratio of minimum to maximum transmission is 0.8766.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       platelike
_exptl_crystal_F_000             436
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 -1.00 0.0530
0.00 0.00 1.00 0.0250
0.00 0.00 -1.00 0.0150
-1.00 -1.00 1.00 0.0650
1.00 -1.00 1.00 0.0080
0.00 1.00 -1.00 0.0020

_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            29258
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         1.771
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2217
_reflns_number_total             2834
_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 (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.006(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         2834
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0491P)²+0.4961P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1156
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Riding coordinates:
 O1(H1)
;
_atom_sites_solution_hydrogens   difmap
_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
B1 B 0.4428(4) 0.0914(2) 0.6475(2) 0.0285(5) Uani 1 1 d . . . . .
B2 B 0.4299(4) 0.3027(2) 0.7520(2) 0.0275(5) Uani 1 1 d . . . . .
B3 B 0.6576(4) 0.2825(2) 0.5953(2) 0.0279(5) Uani 1 1 d . . . . .
F1 F 0.4788(2) 0.33131(13) 0.87280(10) 0.0385(3) Uani 1 1 d . . . . .
F2 F 0.25678(19) 0.36634(13) 0.72628(11) 0.0412(4) Uani 1 1 d . . . . .
F3 F 0.85420(19) 0.26771(14) 0.62730(13) 0.0442(4) Uani 1 1 d . . . . .
F4 F 0.6544(2) 0.35543(13) 0.48944(11) 0.0404(4) Uani 1 1 d . . . . .
O1 O 0.3778(3) -0.04080(15) 0.63708(13) 0.0383(4) Uani 1 1 d . . . . .
H1 H 0.4023 -0.0786 0.5678 0.046 Uiso 1 1 d R U . . .
O2 O 0.3872(2) 0.15937(14) 0.73938(13) 0.0357(4) Uani 1 1 d . . . . .
O3 O 0.5772(2) 0.35628(14) 0.68319(13) 0.0321(4) Uani 1 1 d . . . . .
O4 O 0.5591(2) 0.15085(14) 0.57065(12) 0.0306(4) Uani 1 1 d . . . . .
C1 C 0.8817(3) 0.2872(2) 0.97964(17) 0.0264(5) Uani 1 1 d . . . . .
C2 C 0.7677(3) 0.0909(2) 1.05658(18) 0.0274(5) Uani 1 1 d . . . . .
C3 C 0.7951(3) 0.2920(2) 1.16486(17) 0.0259(4) Uani 1 1 d . . . . .
N1 N 0.9577(3) 0.3520(2) 0.89252(17) 0.0355(5) Uani 1 1 d . . . . .
H2 H 1.010(4) 0.441(3) 0.903(2) 0.043 Uiso 1 1 d . U . . .
H3 H 0.967(4) 0.311(3) 0.828(2) 0.043 Uiso 1 1 d . U . . .
N2 N 0.8314(3) 0.15507(17) 0.96516(15) 0.0294(4) Uani 1 1 d . . . . .
N3 N 0.7206(3) -0.03870(19) 1.05264(19) 0.0367(5) Uani 1 1 d . . . . .
H4 H 0.735(4) -0.084(3) 0.982(2) 0.044 Uiso 1 1 d . U . . .
H5 H 0.684(4) -0.077(3) 1.115(2) 0.044 Uiso 1 1 d . U . . .
N4 N 0.7488(3) 0.15780(17) 1.15852(16) 0.0288(4) Uani 1 1 d . . . . .
H6 H 0.709(3) 0.115(2) 1.224(2) 0.035 Uiso 1 1 d . U . . .
N5 N 0.7723(3) 0.3532(2) 1.26398(16) 0.0347(5) Uani 1 1 d . . . . .
H7 H 0.730(4) 0.307(3) 1.326(2) 0.042 Uiso 1 1 d . U . . .
H8 H 0.787(4) 0.440(3) 1.266(2) 0.042 Uiso 1 1 d . U . . .
N6 N 0.8633(3) 0.36020(16) 1.07679(14) 0.0271(4) Uani 1 1 d . . . . .
C4 C 0.1788(3) 0.1259(2) 0.26626(18) 0.0292(5) Uani 1 1 d . . . . .
C5 C 0.2043(3) 0.3117(2) 0.37862(18) 0.0294(5) Uani 1 1 d . . . . .
C6 C 0.2953(3) 0.3197(2) 0.18679(17) 0.0266(5) Uani 1 1 d . . . . .
N7 N 0.1329(3) -0.00404(19) 0.25505(19) 0.0392(5) Uani 1 1 d . . . . .
H9 H 0.150(4) -0.047(3) 0.187(2) 0.047 Uiso 1 1 d . U . . .
H10 H 0.098(4) -0.045(3) 0.316(3) 0.047 Uiso 1 1 d . U . . .
N8 N 0.1519(3) 0.18210(18) 0.36881(15) 0.0338(4) Uani 1 1 d . . . . .
N9 N 0.1777(3) 0.3767(2) 0.47479(17) 0.0396(5) Uani 1 1 d . . . . .
H11 H 0.126(4) 0.333(3) 0.538(2) 0.048 Uiso 1 1 d . U . . .
H12 H 0.234(4) 0.464(3) 0.488(2) 0.048 Uiso 1 1 d . U . . .
N10 N 0.2819(3) 0.38264(19) 0.29003(15) 0.0294(4) Uani 1 1 d . . . . .
H13 H 0.324(3) 0.469(3) 0.299(2) 0.035 Uiso 1 1 d . U . . .
N11 N 0.3608(3) 0.3925(2) 0.10090(17) 0.0340(5) Uani 1 1 d . . . . .
H14 H 0.400(4) 0.476(3) 0.110(2) 0.041 Uiso 1 1 d . U . . .
H15 H 0.370(4) 0.354(3) 0.032(2) 0.041 Uiso 1 1 d . U . . .
N12 N 0.2450(3) 0.19038(17) 0.17208(15) 0.0295(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
B1 O1 1.367(3) . ?
B1 O2 1.356(3) . ?
B1 O4 1.353(3) . ?
B2 F1 1.434(3) . ?
B2 F2 1.424(3) . ?
B2 O2 1.448(3) . ?
B2 O3 1.418(3) . ?
B3 F3 1.418(3) . ?
B3 F4 1.423(3) . ?
B3 O3 1.427(3) . ?
B3 O4 1.457(3) . ?
O1 H1 0.9165 . ?
C1 N1 1.318(3) . ?
C1 N2 1.349(3) . ?
C1 N6 1.356(3) . ?
C2 N2 1.322(3) . ?
C2 N3 1.313(3) . ?
C2 N4 1.372(3) . ?
C3 N4 1.357(3) . ?
C3 N5 1.322(3) . ?
C3 N6 1.321(3) . ?
N1 H2 0.94(3) . ?
N1 H3 0.85(3) . ?
N3 H4 0.94(3) . ?
N3 H5 0.86(3) . ?
N4 H6 0.92(3) . ?
N5 H7 0.91(3) . ?
N5 H8 0.86(3) . ?
C4 N7 1.320(3) . ?
C4 N8 1.341(3) . ?
C4 N12 1.355(3) . ?
C5 N8 1.323(3) . ?
C5 N9 1.317(3) . ?
C5 N10 1.365(3) . ?
C6 N10 1.359(3) . ?
C6 N11 1.318(3) . ?
C6 N12 1.322(3) . ?
N7 H9 0.91(3) . ?
N7 H10 0.86(3) . ?
N9 H11 0.93(3) . ?
N9 H12 0.94(3) . ?
N10 H13 0.90(3) . ?
N11 H14 0.86(3) . ?
N11 H15 0.89(3) . ?

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
O2 B1 O1 116.73(19) . . ?
O4 B1 O1 121.63(19) . . ?
O4 B1 O2 121.64(19) . . ?
F1 B2 O2 107.83(17) . . ?
F2 B2 F1 104.37(17) . . ?
F2 B2 O2 108.31(18) . . ?
O3 B2 F1 110.73(17) . . ?
O3 B2 F2 110.88(18) . . ?
O3 B2 O2 114.21(18) . . ?
F3 B3 F4 105.69(18) . . ?
F3 B3 O3 109.66(18) . . ?
F3 B3 O4 109.22(18) . . ?
F4 B3 O3 110.16(18) . . ?
F4 B3 O4 107.53(17) . . ?
O3 B3 O4 114.21(18) . . ?
B1 O1 H1 113.4 . . ?
B1 O2 B2 121.38(17) . . ?
B2 O3 B3 123.97(16) . . ?
B1 O4 B3 120.70(17) . . ?
N1 C1 N2 117.63(19) . . ?
N1 C1 N6 116.45(18) . . ?
N2 C1 N6 125.92(18) . . ?
N2 C2 N4 120.92(18) . . ?
N3 C2 N2 121.06(19) . . ?
N3 C2 N4 118.02(19) . . ?
N5 C3 N4 117.54(19) . . ?
N6 C3 N4 122.08(18) . . ?
N6 C3 N5 120.36(19) . . ?
C1 N1 H2 119.6(16) . . ?
C1 N1 H3 119.6(18) . . ?
H2 N1 H3 121(2) . . ?
C2 N2 C1 116.28(17) . . ?
C2 N3 H4 117.5(16) . . ?
C2 N3 H5 117.6(18) . . ?
H4 N3 H5 125(2) . . ?
C2 N4 H6 122.5(15) . . ?
C3 N4 C2 119.31(18) . . ?
C3 N4 H6 118.1(15) . . ?
C3 N5 H7 121.5(16) . . ?
C3 N5 H8 117.8(18) . . ?
H7 N5 H8 120(2) . . ?
C3 N6 C1 115.39(17) . . ?
N7 C4 N8 117.0(2) . . ?
N7 C4 N12 116.79(19) . . ?
N8 C4 N12 126.23(19) . . ?
N8 C5 N10 121.87(19) . . ?
N9 C5 N8 120.0(2) . . ?
N9 C5 N10 118.1(2) . . ?
N11 C6 N10 117.44(19) . . ?
N11 C6 N12 120.77(19) . . ?
N12 C6 N10 121.79(19) . . ?
C4 N7 H9 120.3(17) . . ?
C4 N7 H10 116.3(19) . . ?
H9 N7 H10 123(3) . . ?
C5 N8 C4 115.58(18) . . ?
C5 N9 H11 121.8(16) . . ?
C5 N9 H12 120.7(17) . . ?
H11 N9 H12 116(2) . . ?
C5 N10 H13 121.1(15) . . ?
C6 N10 C5 118.82(18) . . ?
C6 N10 H13 120.0(15) . . ?
C6 N11 H14 122.2(18) . . ?
C6 N11 H15 119.2(17) . . ?
H14 N11 H15 119(2) . . ?
C6 N12 C4 115.52(17) . . ?

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
O1 H1 O4 0.92 1.80 2.715(2) 177.6 2_656
N3 H5 O2 0.86(3) 1.95(3) 2.811(3) 177(3) 2_657
N4 H6 O1 0.92(3) 1.88(3) 2.803(2) 175(2) 2_657
N5 H7 F4 0.91(3) 2.06(3) 2.784(2) 136(2) 1_556
N5 H8 F2 0.86(3) 1.99(3) 2.832(2) 164(2) 2_667
N9 H12 F4 0.94(3) 1.92(3) 2.860(2) 178(2) 2_666
N10 H13 O3 0.90(3) 1.83(3) 2.730(2) 177(2) 2_666
N11 H15 F1 0.89(3) 2.05(3) 2.892(2) 155(2) 1_554

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
F1 B2 O2 B1 -141.2(2) . . . . ?
F1 B2 O3 B3 131.4(2) . . . . ?
F2 B2 O2 B1 106.4(2) . . . . ?
F2 B2 O3 B3 -113.2(2) . . . . ?
F3 B3 O3 B2 -115.4(2) . . . . ?
F3 B3 O4 B1 104.7(2) . . . . ?
F4 B3 O3 B2 128.6(2) . . . . ?
F4 B3 O4 B1 -141.1(2) . . . . ?
O1 B1 O2 B2 -173.2(2) . . . . ?
O1 B1 O4 B3 -167.6(2) . . . . ?
O2 B1 O4 B3 11.5(3) . . . . ?
O2 B2 O3 B3 9.5(3) . . . . ?
O3 B2 O2 B1 -17.7(3) . . . . ?
O3 B3 O4 B1 -18.5(3) . . . . ?
O4 B1 O2 B2 7.7(3) . . . . ?
O4 B3 O3 B2 7.5(3) . . . . ?
N1 C1 N2 C2 175.6(2) . . . . ?
N1 C1 N6 C3 -177.0(2) . . . . ?
N2 C1 N6 C3 2.2(3) . . . . ?
N2 C2 N4 C3 0.5(3) . . . . ?
N3 C2 N2 C1 -177.9(2) . . . . ?
N3 C2 N4 C3 -179.5(2) . . . . ?
N4 C2 N2 C1 2.1(3) . . . . ?
N4 C3 N6 C1 0.7(3) . . . . ?
N5 C3 N4 C2 179.0(2) . . . . ?
N5 C3 N6 C1 179.67(19) . . . . ?
N6 C1 N2 C2 -3.6(3) . . . . ?
N6 C3 N4 C2 -2.0(3) . . . . ?
N7 C4 N8 C5 178.1(2) . . . . ?
N7 C4 N12 C6 -178.1(2) . . . . ?
N8 C4 N12 C6 3.4(3) . . . . ?
N8 C5 N10 C6 3.7(3) . . . . ?
N9 C5 N8 C4 177.8(2) . . . . ?
N9 C5 N10 C6 -174.5(2) . . . . ?
N10 C5 N8 C4 -0.4(3) . . . . ?
N10 C6 N12 C4 0.3(3) . . . . ?
N11 C6 N10 C5 176.3(2) . . . . ?
N11 C6 N12 C4 -179.6(2) . . . . ?
N12 C4 N8 C5 -3.3(3) . . . . ?
N12 C6 N10 C5 -3.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
