# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_111
_database_code_depnum_ccdc_archive 'CCDC 2292113'
loop_
_audit_author_name
_audit_author_address
'Miriding Mutailipu'
;Chinese academic of science
China
;
_audit_update_record             
;
2023-09-02 deposited with the CCDC.	2023-09-20 downloaded from the CCDC.
;
_audit_creation_date             2023-04-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'B3 F4 H O4, C H6 N3, H4 N'
_chemical_formula_sum            'C H11 B3 F4 N4 O4'
_chemical_formula_weight         251.57
_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.280(2)
_cell_length_b                   8.7593(11)
_cell_length_c                   14.8039(18)
_cell_angle_alpha                90
_cell_angle_beta                 98.748(9)
_cell_angle_gamma                90
_cell_volume                     1958.4(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4985
_cell_measurement_temperature    156.0
_cell_measurement_theta_max      24.41
_cell_measurement_theta_min      2.69
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6013
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1561 before and 0.0752 after correction.
The Ratio of minimum to maximum transmission is 0.8065.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0949
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31760
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_min         2.688
_diffrn_ambient_temperature      156.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.996
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1702
_reflns_number_total             2254
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.398
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2254
_refine_ls_number_restraints     55
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.064
_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)+(0.0319P)²+2.5029P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1067
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
2. Restrained distances
 N4-H1 = N4-H2 = N4-H3 = N4-H11
 0.85 with sigma of 0.02
 N4-H1 \\sim N4-H2 \\sim N4-H3 \\sim N4-H11
 with sigma of 0.02
 H1-H2 \\sim H2-H3 \\sim H3-H11 \\sim H11-H1 \\sim H2-H11 \\sim H1-H3
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
N4 \\sim H1 \\sim H2 \\sim H3 \\sim H11: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 N4, H1, H2, H3, H11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a X=CH2 refined with riding coordinates:
 N3(H5,H4), N2(H8,H9), N1(H6,H7)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
F3 F 0.74073(9) 0.70676(15) 0.74557(9) 0.0519(4) Uani 1 1 d . . . . .
F1 F 0.92473(8) 0.39533(14) 0.67635(9) 0.0494(3) Uani 1 1 d . . . . .
F2 F 0.92526(8) 0.53102(17) 0.54808(9) 0.0534(4) Uani 1 1 d . . . . .
O2 O 0.79816(7) 0.39429(14) 0.56605(9) 0.0318(3) Uani 1 1 d . . . . .
O4 O 0.64907(8) 0.31109(15) 0.55062(10) 0.0340(3) Uani 1 1 d . . . . .
O1 O 0.68946(8) 0.53956(14) 0.62666(10) 0.0342(3) Uani 1 1 d . . . . .
F4 F 0.73050(10) 0.79460(15) 0.60065(11) 0.0638(4) Uani 1 1 d . . . . .
O3 O 0.84220(8) 0.61698(15) 0.65767(10) 0.0393(4) Uani 1 1 d . . . . .
N3 N 0.50685(10) 0.61147(19) 0.63428(13) 0.0423(4) Uani 1 1 d . . . . .
H5 H 0.559280 0.595646 0.618337 0.051 Uiso 1 1 calc R U . . .
H4 H 0.492829 0.702573 0.652649 0.051 Uiso 1 1 calc R U . . .
N2 N 0.37034(11) 0.5221(2) 0.65357(14) 0.0473(5) Uani 1 1 d . . . . .
H8 H 0.331906 0.446749 0.650461 0.057 Uiso 1 1 calc R U . . .
H9 H 0.356057 0.613027 0.671973 0.057 Uiso 1 1 calc R U . . .
N1 N 0.47039(12) 0.3625(2) 0.60316(15) 0.0517(5) Uani 1 1 d . . . . .
H6 H 0.522842 0.346795 0.587228 0.062 Uiso 1 1 calc R U . . .
H7 H 0.432020 0.287135 0.600709 0.062 Uiso 1 1 calc R U . . .
C1 C 0.44932(12) 0.4987(2) 0.63065(13) 0.0329(4) Uani 1 1 d . . . . .
B2 B 0.86908(12) 0.4893(2) 0.61161(14) 0.0286(4) Uani 1 1 d . . . . .
B1 B 0.71324(12) 0.4161(2) 0.58153(13) 0.0271(4) Uani 1 1 d . . . . .
B3 B 0.75235(13) 0.6611(2) 0.65670(14) 0.0286(4) Uani 1 1 d . . . . .
H10 H 0.6633(17) 0.253(3) 0.5127(18) 0.054(7) Uiso 1 1 d . . . . .
N4 N 0.61098(11) 1.0215(2) 0.64805(12) 0.0344(4) Uani 1 1 d D U . . .
H1 H 0.627(2) 1.103(2) 0.628(2) 0.097(10) Uiso 1 1 d D U . . .
H2 H 0.5607(10) 1.005(3) 0.6244(18) 0.082(9) Uiso 1 1 d D U . . .
H3 H 0.6439(16) 0.954(2) 0.6340(19) 0.078(9) Uiso 1 1 d D U . . .
H11 H 0.615(2) 1.029(3) 0.7035(9) 0.091(9) Uiso 1 1 d D U . . .


_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
F3 B3 1.412(2) . ?
F1 B2 1.439(2) . ?
F2 B2 1.414(2) . ?
O2 B2 1.449(2) . ?
O2 B1 1.365(2) . ?
O4 B1 1.371(2) . ?
O4 H10 0.81(3) . ?
O1 B1 1.350(2) . ?
O1 B3 1.458(2) . ?
F4 B3 1.443(2) . ?
O3 B2 1.403(2) . ?
O3 B3 1.424(2) . ?
N3 H5 0.8800 . ?
N3 H4 0.8800 . ?
N3 C1 1.318(2) . ?
N2 H8 0.8800 . ?
N2 H9 0.8800 . ?
N2 C1 1.318(2) . ?
N1 H6 0.8800 . ?
N1 H7 0.8800 . ?
N1 C1 1.317(2) . ?
N4 H1 0.823(13) . ?
N4 H2 0.808(12) . ?
N4 H3 0.821(12) . ?
N4 H11 0.816(12) . ?

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 B2 120.28(14) . . ?
B1 O4 H10 113.6(19) . . ?
B1 O1 B3 121.45(14) . . ?
B2 O3 B3 124.36(14) . . ?
H5 N3 H4 120.0 . . ?
C1 N3 H5 120.0 . . ?
C1 N3 H4 120.0 . . ?
H8 N2 H9 120.0 . . ?
C1 N2 H8 120.0 . . ?
C1 N2 H9 120.0 . . ?
H6 N1 H7 120.0 . . ?
C1 N1 H6 120.0 . . ?
C1 N1 H7 120.0 . . ?
N3 C1 N2 120.29(18) . . ?
N1 C1 N3 119.93(17) . . ?
N1 C1 N2 119.78(18) . . ?
F1 B2 O2 107.80(15) . . ?
F2 B2 F1 103.51(14) . . ?
F2 B2 O2 108.99(15) . . ?
O3 B2 F1 108.61(15) . . ?
O3 B2 F2 111.67(16) . . ?
O3 B2 O2 115.50(14) . . ?
O2 B1 O4 120.00(16) . . ?
O1 B1 O2 121.97(15) . . ?
O1 B1 O4 118.03(16) . . ?
F3 B3 O1 108.70(15) . . ?
F3 B3 F4 104.82(15) . . ?
F3 B3 O3 108.97(15) . . ?
F4 B3 O1 109.40(15) . . ?
O3 B3 O1 113.22(14) . . ?
O3 B3 F4 111.36(16) . . ?
H1 N4 H2 108(2) . . ?
H1 N4 H3 108(2) . . ?
H1 N4 H11 108(2) . . ?
H2 N4 H3 110(2) . . ?
H2 N4 H11 112(2) . . ?
H3 N4 H11 111(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
B2 O2 B1 O4 -169.22(16) . . . . ?
B2 O2 B1 O1 11.0(3) . . . . ?
B2 O3 B3 F3 138.25(18) . . . . ?
B2 O3 B3 O1 17.2(3) . . . . ?
B2 O3 B3 F4 -106.6(2) . . . . ?
B1 O2 B2 F1 111.00(18) . . . . ?
B1 O2 B2 F2 -137.29(17) . . . . ?
B1 O2 B2 O3 -10.6(3) . . . . ?
B1 O1 B3 F3 -138.18(17) . . . . ?
B1 O1 B3 F4 107.90(19) . . . . ?
B1 O1 B3 O3 -16.9(3) . . . . ?
B3 O1 B1 O2 3.7(3) . . . . ?
B3 O1 B1 O4 -176.12(16) . . . . ?
B3 O3 B2 F1 -125.37(18) . . . . ?
B3 O3 B2 F2 121.11(19) . . . . ?
B3 O3 B2 O2 -4.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
