# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_mo_WSU_ZH43_0m
_database_code_depnum_ccdc_archive 'CCDC 1920026'
loop_
_audit_author_name
_audit_author_address
'Zachariah Heiden'
;Washington State University
United States of America
;
_audit_update_record             
;
2019-07-25 deposited with the CCDC.	2019-07-30 downloaded from the CCDC.
;
_audit_creation_date             2019-07-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_chemical_formula_moiety         'C15 H13 B F2 N4'
_chemical_formula_sum            'C15 H13 B F2 N4'
_chemical_formula_weight         298.12
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.1533(6)
_cell_length_b                   16.1324(12)
_cell_length_c                   10.8149(8)
_cell_angle_alpha                90
_cell_angle_beta                 111.027(3)
_cell_angle_gamma                90
_cell_volume                     1327.79(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9234
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.96
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7036
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0504 before and 0.0473 after correction.
The Ratio of minimum to maximum transmission is 0.9437.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.4911
_exptl_crystal_description       Prism
_exptl_crystal_F_000             616.3137
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21974
_diffrn_reflns_theta_full        27.5436
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.96
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.9987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71076
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -10
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              -6
_reflns_number_gt                2555
_reflns_number_total             3064
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.4370
_refine_diff_density_min         -0.2612
_refine_diff_density_rms         0.0627
_refine_ls_d_res_high            0.7685
_refine_ls_d_res_low             6.8830
_refine_ls_goodness_of_fit_ref   1.0547
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3064
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.0547
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+0.5933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0962
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C1(H1), C2(H2), C3(H3a), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13),
 C14(H14), C15(H15)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
F1 F 0.20412(11) 0.37953(5) 0.32277(8) 0.0251(2) Uani 1.000000 .
F2 F 0.21008(10) 0.41358(5) 0.12207(8) 0.02152(19) Uani 1.000000 .
N1 N 0.47123(14) 0.44023(7) 0.31245(11) 0.0171(2) Uani 1.000000 .
N2 N 0.20412(14) 0.52501(7) 0.27002(11) 0.0175(2) Uani 1.000000 .
N3 N 0.59768(14) 0.65367(7) 0.39924(11) 0.0177(2) Uani 1.000000 .
H3 H 0.70772(14) 0.64266(7) 0.42144(11) 0.0212(3) Uiso 1.000000 R
N4 N 0.87285(14) 0.74917(7) 0.47156(11) 0.0185(2) Uani 1.000000 .
C1 C 0.58342(18) 0.37727(8) 0.31700(13) 0.0201(3) Uani 1.000000 .
H1 H 0.54986(18) 0.32298(8) 0.29122(13) 0.0241(3) Uiso 1.000000 R
C2 C 0.75501(18) 0.40549(8) 0.36554(14) 0.0214(3) Uani 1.000000 .
H2 H 0.85568(18) 0.37434(8) 0.37806(14) 0.0256(3) Uiso 1.000000 R
C3 C 0.74773(17) 0.48980(8) 0.39209(13) 0.0191(3) Uani 1.000000 .
H3a H 0.84304(17) 0.52545(8) 0.42615(13) 0.0229(3) Uiso 1.000000 R
C4 C 0.57163(17) 0.51056(8) 0.35817(12) 0.0161(3) Uani 1.000000 .
C5 C 0.49126(16) 0.58969(8) 0.35928(12) 0.0153(3) Uani 1.000000 .
C6 C 0.30454(17) 0.59578(8) 0.31525(12) 0.0165(3) Uani 1.000000 .
C7 C 0.19025(17) 0.66225(9) 0.30584(14) 0.0209(3) Uani 1.000000 .
H7 H 0.22202(17) 0.71705(9) 0.32902(14) 0.0251(3) Uiso 1.000000 R
C8 C 0.01988(18) 0.63075(9) 0.25518(15) 0.0248(3) Uani 1.000000 .
H8 H -0.08356(18) 0.66048(9) 0.23853(15) 0.0297(4) Uiso 1.000000 R
C9 C 0.03381(17) 0.54677(9) 0.23432(14) 0.0222(3) Uani 1.000000 .
H9 H -0.06068(17) 0.51063(9) 0.20056(14) 0.0266(4) Uiso 1.000000 R
C10 C 0.55610(17) 0.73978(8) 0.41114(13) 0.0180(3) Uani 1.000000 .
H10a H 0.47955(17) 0.76065(8) 0.32582(13) 0.0216(3) Uiso 1.000000 R
H10b H 0.49541(17) 0.74507(8) 0.47320(13) 0.0216(3) Uiso 1.000000 R
C11 C 0.72496(16) 0.78950(8) 0.45959(12) 0.0156(3) Uani 1.000000 .
C12 C 0.72030(17) 0.87298(8) 0.48979(13) 0.0171(3) Uani 1.000000 .
H12 H 0.61463(17) 0.89885(8) 0.48062(13) 0.0205(3) Uiso 1.000000 R
C13 C 0.87680(17) 0.91668(8) 0.53387(13) 0.0181(3) Uani 1.000000 .
H13 H 0.87817(17) 0.97272(8) 0.55444(13) 0.0217(3) Uiso 1.000000 R
C14 C 1.03143(17) 0.87561(8) 0.54686(13) 0.0187(3) Uani 1.000000 .
H14 H 1.13848(17) 0.90341(8) 0.57651(13) 0.0224(3) Uiso 1.000000 R
C15 C 1.02294(17) 0.79257(8) 0.51481(14) 0.0202(3) Uani 1.000000 .
H15 H 1.12697(17) 0.76522(8) 0.52368(14) 0.0242(3) Uiso 1.000000 R
B1 B 0.26929(19) 0.43683(9) 0.25566(15) 0.0179(3) Uani 1.000000 .


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 B1 1.3929(17) . ?
F2 B1 1.4002(17) . ?
N1 C1 1.3558(17) . ?
N1 C4 1.3826(16) . ?
N1 B1 1.5380(18) . ?
N2 C6 1.3877(16) . ?
N2 C9 1.3475(17) . ?
N2 B1 1.5458(18) . ?
N3 C5 1.3176(16) . ?
N3 C10 1.4466(16) . ?
N4 C11 1.3350(16) . ?
N4 C15 1.3400(17) . ?
C1 C2 1.3832(19) . ?
C2 C3 1.3957(19) . ?
C3 C4 1.3894(18) . ?
C4 C5 1.4369(18) . ?
C5 C6 1.4262(18) . ?
C6 C7 1.4001(18) . ?
C7 C8 1.3935(19) . ?
C8 C9 1.385(2) . ?
C10 C11 1.5152(17) . ?
C11 C12 1.3894(18) . ?
C12 C13 1.3842(18) . ?
C13 C14 1.3861(19) . ?
C14 C15 1.3794(19) . ?

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
C4 N1 C1 107.25(11) . . ?
B1 N1 C1 126.82(11) . . ?
B1 N1 C4 125.71(11) . . ?
C9 N2 C6 107.67(11) . . ?
B1 N2 C6 127.73(11) . . ?
B1 N2 C9 124.54(11) . . ?
C10 N3 C5 129.33(11) . . ?
C15 N4 C11 117.33(11) . . ?
C2 C1 N1 110.15(12) . . ?
C3 C2 C1 106.68(12) . . ?
C4 C3 C2 107.26(12) . . ?
C3 C4 N1 108.65(11) . . ?
C5 C4 N1 121.25(11) . . ?
C5 C4 C3 130.03(12) . . ?
C4 C5 N3 116.75(11) . . ?
C6 C5 N3 123.64(12) . . ?
C6 C5 C4 119.59(11) . . ?
C5 C6 N2 119.02(11) . . ?
C7 C6 N2 108.14(11) . . ?
C7 C6 C5 132.84(12) . . ?
C8 C7 C6 107.03(12) . . ?
C9 C8 C7 107.00(12) . . ?
C8 C9 N2 110.16(12) . . ?
C11 C10 N3 109.04(10) . . ?
C10 C11 N4 116.91(11) . . ?
C12 C11 N4 123.34(12) . . ?
C12 C11 C10 119.75(11) . . ?
C13 C12 C11 118.36(12) . . ?
C14 C13 C12 118.95(12) . . ?
C15 C14 C13 118.49(12) . . ?
C14 C15 N4 123.53(12) . . ?
F2 B1 F1 107.77(11) . . ?
N1 B1 F1 111.68(11) . . ?
N1 B1 F2 110.18(11) . . ?
N2 B1 F1 110.44(11) . . ?
N2 B1 F2 110.27(11) . . ?
N2 B1 N1 106.52(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_WSU_ZH37
_database_code_depnum_ccdc_archive 'CCDC 1920027'
loop_
_audit_author_name
_audit_author_address
'Zachariah Heiden'
;Washington State University
United States of America
;
_audit_update_record             
;
2019-07-25 deposited with the CCDC.	2019-07-30 downloaded from the CCDC.
;
_audit_creation_date             2019-05-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_chemical_formula_moiety         'C9 H9 B F2 N4'
_chemical_formula_sum            'C9 H9 B F2 N4'
_chemical_formula_weight         222.02
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   6.2353(4)
_cell_length_b                   13.4196(9)
_cell_length_c                   11.5682(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.876(2)
_cell_angle_gamma                90
_cell_volume                     953.63(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5567
_cell_measurement_theta_max      26.30
_cell_measurement_theta_min      3.04
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0431 before and 0.0405 after correction.
The Ratio of minimum to maximum transmission is 0.9391.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.5462
_exptl_crystal_description       plate
_exptl_crystal_F_000             456.2504
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15161
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         3.04
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1688
_reflns_number_total             1966
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.3144
_refine_diff_density_min         -0.2499
_refine_diff_density_rms         0.0565
_refine_ls_d_res_high            0.7987
_refine_ls_d_res_low             6.7098
_refine_ls_goodness_of_fit_ref   1.0563
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1966
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0325
_refine_ls_restrained_S_all      1.0563
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+0.4760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0825
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Rotating group:
 N4(H4a)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), N3(H3a), C7(H7), C8(H8), C9(H9)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
F1 F 0.79876(13) 0.73098(6) 0.29802(7) 0.0202(2) Uani 1.000000 .
C1 C 0.6632(2) 0.65424(10) 0.04132(12) 0.0179(3) Uani 1.000000 .
H1 H 0.7785(2) 0.61014(10) 0.06174(12) 0.0215(4) Uiso 1.000000 R
N1 N 0.64494(18) 0.74338(8) 0.09252(9) 0.0144(2) Uani 1.000000 .
B1 B 0.8082(2) 0.78535(11) 0.19641(13) 0.0155(3) Uani 1.000000 .
F2 F 1.01961(13) 0.77852(6) 0.17264(7) 0.0222(2) Uani 1.000000 .
N2 N 0.74432(17) 0.89438(8) 0.21137(9) 0.0145(2) Uani 1.000000 .
C2 C 0.4853(2) 0.63790(10) -0.04603(12) 0.0186(3) Uani 1.000000 .
H2 H 0.4607(2) 0.58206(10) -0.09409(12) 0.0224(4) Uiso 1.000000 R
C3 C 0.3507(2) 0.72030(10) -0.04848(12) 0.0167(3) Uani 1.000000 .
H3 H 0.2188(2) 0.72999(10) -0.09849(12) 0.0200(3) Uiso 1.000000 R
N3 N 0.21402(17) 0.93019(8) 0.03337(10) 0.0150(2) Uani 1.000000 .
H3a H 0.20118(17) 0.99011(8) 0.05767(10) 0.0180(3) Uiso 1.000000 R
N4 N 0.03760(18) 0.89224(9) -0.04690(10) 0.0172(3) Uani 1.000000 .
H4a H -0.00074(18) 0.83551(9) -0.02249(10) 0.0207(3) Uiso 1.000000 GR
C4 C 0.4504(2) 0.78663(10) 0.03865(11) 0.0135(3) Uani 1.000000 .
C5 C 0.3970(2) 0.88342(9) 0.07523(11) 0.0129(3) Uani 1.000000 .
C6 C 0.5492(2) 0.93729(9) 0.16122(11) 0.0132(3) Uani 1.000000 .
C7 C 0.5404(2) 1.03343(10) 0.20479(11) 0.0157(3) Uani 1.000000 .
H7 H 0.4272(2) 1.07880(10) 0.18537(11) 0.0188(3) Uiso 1.000000 R
C8 C 0.7347(2) 1.04897(10) 0.28355(12) 0.0184(3) Uani 1.000000 .
H8 H 0.7751(2) 1.10667(10) 0.32629(12) 0.0220(4) Uiso 1.000000 R
C9 C 0.8547(2) 0.96238(10) 0.28570(12) 0.0185(3) Uani 1.000000 .
H9 H 0.9909(2) 0.95214(10) 0.33129(12) 0.0222(4) Uiso 1.000000 R
H4b H 0.081(3) 0.8816(14) -0.1177(17) 0.033(5) Uiso 1.000000 .


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 B1 1.3932(17) . ?
C1 H1 0.9300 . ?
C1 N1 1.3482(17) . ?
C1 C2 1.384(2) . ?
N1 B1 1.5422(18) . ?
N1 C4 1.3919(17) . ?
B1 F2 1.3950(17) . ?
B1 N2 1.5339(18) . ?
N2 C6 1.3808(16) . ?
N2 C9 1.3575(17) . ?
C2 H2 0.9300 . ?
C2 C3 1.3853(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.4069(18) . ?
N3 H3a 0.8600 . ?
N3 N4 1.4076(15) . ?
N3 C5 1.3195(17) . ?
N4 H4a 0.8600 . ?
N4 H4b 0.915(19) . ?
C4 C5 1.4231(18) . ?
C5 C6 1.4450(18) . ?
C6 C7 1.3896(18) . ?
C7 H7 0.9300 . ?
C7 C8 1.4008(19) . ?
C8 H8 0.9300 . ?
C8 C9 1.380(2) . ?
C9 H9 0.9300 . ?

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
N1 C1 H1 124.94(8) . . ?
C2 C1 H1 124.94(8) . . ?
C2 C1 N1 110.12(12) . . ?
B1 N1 C1 124.91(11) . . ?
C4 N1 C1 107.82(11) . . ?
C4 N1 B1 127.20(11) . . ?
N1 B1 F1 110.39(11) . . ?
F2 B1 F1 108.06(11) . . ?
F2 B1 N1 110.00(11) . . ?
N2 B1 F1 110.80(11) . . ?
N2 B1 N1 106.67(10) . . ?
N2 B1 F2 110.94(11) . . ?
C6 N2 B1 125.28(11) . . ?
C9 N2 B1 126.83(11) . . ?
C9 N2 C6 107.47(11) . . ?
H2 C2 C1 126.41(8) . . ?
C3 C2 C1 107.17(12) . . ?
C3 C2 H2 126.41(8) . . ?
H3 C3 C2 126.31(8) . . ?
C4 C3 C2 107.38(12) . . ?
C4 C3 H3 126.31(8) . . ?
N4 N3 H3a 116.61(6) . . ?
C5 N3 H3a 116.61(7) . . ?
C5 N3 N4 126.78(11) . . ?
H4a N4 N3 109.5 . . ?
H4b N4 N3 109.3(11) . . ?
H4b N4 H4a 107.2(11) . . ?
C3 C4 N1 107.51(11) . . ?
C5 C4 N1 118.54(11) . . ?
C5 C4 C3 133.90(12) . . ?
C4 C5 N3 123.82(12) . . ?
C6 C5 N3 116.04(11) . . ?
C6 C5 C4 120.13(11) . . ?
C5 C6 N2 120.51(11) . . ?
C7 C6 N2 108.75(11) . . ?
C7 C6 C5 130.71(12) . . ?
H7 C7 C6 126.55(8) . . ?
C8 C7 C6 106.90(12) . . ?
C8 C7 H7 126.55(8) . . ?
H8 C8 C7 126.51(8) . . ?
C9 C8 C7 106.99(12) . . ?
C9 C8 H8 126.51(8) . . ?
C8 C9 N2 109.89(12) . . ?
H9 C9 N2 125.06(7) . . ?
H9 C9 C8 125.06(8) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
