# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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 2302181'
loop_
_audit_author_name
_audit_author_address
'Douglas Stephan'
;University of Toronto
Canada
;
_audit_update_record             
;
2023-10-19 deposited with the CCDC.	2023-11-30 downloaded from the CCDC.
;
_audit_creation_date             2023-09-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'C13 H23 B N O2'
_chemical_formula_sum            'C13 H23 B N O2'
_chemical_formula_weight         236.157
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
B 0.00156 0.00068 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.19320 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   18.1833(14)
_cell_length_b                   12.0913(14)
_cell_length_c                   12.3509(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.667(8)
_cell_angle_gamma                90
_cell_volume                     2709.9(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6252
_cell_measurement_temperature    150.01
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.24
_exptl_crystal_description       blocks
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7126
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0714 before and 0.0479 after correction.
The Ratio of minimum to maximum transmission is 0.9557.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_density_meas      .
_exptl_crystal_F_000             1032.605
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.9992
_diffrn_reflns_Laue_measured_fraction_max 0.9992
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25630
_diffrn_reflns_point_group_measured_fraction_full 0.9992
_diffrn_reflns_point_group_measured_fraction_max 0.9992
_diffrn_reflns_theta_full        24.9942
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.02
_diffrn_ambient_temperature      150.01
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.9992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              21
_reflns_limit_h_min              -21
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1922
_reflns_number_total             2388
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.6250
_refine_diff_density_min         -0.2473
_refine_diff_density_rms         0.0537
_refine_ls_d_res_high            0.8410
_refine_ls_d_res_low             10.0621
_refine_ls_goodness_of_fit_ref   1.0796
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      1.0796
_refine_ls_shift/su_max          -0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0546P)²+4.2702P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1347
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6a,H6b), C8(H8a,H8b), C11(H11a,H11b), C12(H12a,H12b), C13(H13a,H13b),
 C14(H14a,H14b)
2.c Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c), C3(H3a,H3b,H3c), C2(H2a,H2b,H2c)
;
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
O3 O 0.10258(7) 0.78169(12) 0.05210(11) 0.0295(4) Uani 1.000000 .
O1 O 0.15327(7) 0.66578(11) -0.06825(11) 0.0285(4) Uani 1.000000 .
C4 C 0.15916(10) 0.74216(15) 0.00397(14) 0.0184(4) Uani 1.000000 .
C5 C 0.23207(11) 0.65363(16) -0.23592(15) 0.0241(4) Uani 1.000000 .
H5 H 0.22284(11) 0.73387(16) -0.25100(15) 0.0289(5) Uiso 1.000000 R
C6 C 0.30828(11) 0.62286(18) -0.27387(17) 0.0300(5) Uani 1.000000 .
H6a H 0.30620(11) 0.62716(18) -0.35405(17) 0.0360(6) Uiso 1.000000 R
H6b H 0.34425(11) 0.67890(18) -0.24554(17) 0.0360(6) Uiso 1.000000 R
C7 C 0.24759(11) 0.50593(15) -0.08474(16) 0.0245(4) Uani 1.000000 .
H7 H 0.24840(11) 0.49386(15) -0.00457(16) 0.0294(5) Uiso 1.000000 R
C8 C 0.32320(12) 0.47494(17) -0.12345(18) 0.0324(5) Uani 1.000000 .
H8a H 0.36156(12) 0.50956(17) -0.07401(18) 0.0389(6) Uiso 1.000000 R
H8b H 0.32924(12) 0.39378(17) -0.11708(18) 0.0389(6) Uiso 1.000000 R
B10 B 0.23078(11) 0.63314(17) -0.10889(17) 0.0208(5) Uani 1.000000 .
C11 C 0.16816(12) 0.5855(2) -0.29112(18) 0.0387(6) Uani 1.000000 .
H11a H 0.12092(12) 0.6181(2) -0.27129(18) 0.0465(7) Uiso 1.000000 R
H11b H 0.17024(12) 0.5923(2) -0.37075(18) 0.0465(7) Uiso 1.000000 R
C12 C 0.18353(12) 0.43834(18) -0.13912(19) 0.0382(6) Uani 1.000000 .
H12a H 0.19448(12) 0.35869(18) -0.12884(19) 0.0458(7) Uiso 1.000000 R
H12b H 0.13818(12) 0.45477(18) -0.10185(19) 0.0458(7) Uiso 1.000000 R
C13 C 0.33697(12) 0.50867(19) -0.23966(19) 0.0364(5) Uani 1.000000 .
H13a H 0.31368(12) 0.45309(19) -0.28974(19) 0.0437(7) Uiso 1.000000 R
H13b H 0.39070(12) 0.50651(19) -0.24831(19) 0.0437(7) Uiso 1.000000 R
C14 C 0.16861(13) 0.4609(2) -0.2610(2) 0.0443(6) Uani 1.000000 .
H14a H 0.12033(13) 0.4285(2) -0.2852(2) 0.0532(8) Uiso 1.000000 R
H14b H 0.20680(13) 0.4231(2) -0.3011(2) 0.0532(8) Uiso 1.000000 R
N1 N 0.22488(8) 0.77993(13) 0.03091(13) 0.0215(4) Uani 1.000000 .
C1 C 0.02543(10) 0.76506(16) 0.00562(15) 0.0236(4) Uani 1.000000 .
C9 C -0.01783(12) 0.8343(2) 0.0824(2) 0.0456(7) Uani 1.000000 .
H9a H -0.0122(8) 0.8028(9) 0.1556(4) 0.0684(10) Uiso 1.000000 GR
H9b H 0.0009(6) 0.9103(4) 0.0837(11) 0.0684(10) Uiso 1.000000 GR
H9c H -0.07007(19) 0.8344(12) 0.0574(8) 0.0684(10) Uiso 1.000000 GR
C3 C 0.01840(15) 0.8114(2) -0.10712(19) 0.0498(7) Uani 1.000000 .
H3a H 0.0368(10) 0.8876(6) -0.1063(3) 0.0747(11) Uiso 1.000000 GR
H3b H 0.0473(8) 0.7663(9) -0.1548(4) 0.0747(11) Uiso 1.000000 GR
H3c H -0.03350(19) 0.8106(15) -0.1339(6) 0.0747(11) Uiso 1.000000 GR
C2 C 0.00483(13) 0.6448(2) 0.0109(2) 0.0501(7) Uani 1.000000 .
H2a H 0.0345(7) 0.6022(3) -0.0378(11) 0.0752(10) Uiso 1.000000 GR
H2b H 0.0141(10) 0.6179(4) 0.0853(4) 0.0752(10) Uiso 1.000000 GR
H2c H -0.0475(3) 0.6359(3) -0.0115(15) 0.0752(10) Uiso 1.000000 GR


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
O3 C4 1.311(2) . ?
O3 C1 1.495(2) . ?
O1 C4 1.284(2) . ?
O1 B10 1.576(2) . ?
C4 N1 1.302(2) . ?
C5 H5 1.0000 . ?
C5 C6 1.537(3) . ?
C5 B10 1.590(3) . ?
C5 C11 1.546(3) . ?
C6 H6a 0.9900 . ?
C6 H6b 0.9900 . ?
C6 C13 1.526(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.531(3) . ?
C7 B10 1.593(3) . ?
C7 C12 1.541(3) . ?
C8 H8a 0.9900 . ?
C8 H8b 0.9900 . ?
C8 C13 1.528(3) . ?
B10 N1 1.607(2) 7_565 ?
C11 H11a 0.9900 . ?
C11 H11b 0.9900 . ?
C11 C14 1.552(4) . ?
C12 H12a 0.9900 . ?
C12 H12b 0.9900 . ?
C12 C14 1.537(3) . ?
C13 H13a 0.9900 . ?
C13 H13b 0.9900 . ?
C14 H14a 0.9900 . ?
C14 H14b 0.9900 . ?
N1 N1 1.425(3) 7_565 ?
C1 C9 1.522(3) . ?
C1 C3 1.499(3) . ?
C1 C2 1.504(3) . ?
C9 H9a 0.9800 . ?
C9 H9b 0.9800 . ?
C9 H9c 0.9800 . ?
C3 H3a 0.9800 . ?
C3 H3b 0.9800 . ?
C3 H3c 0.9800 . ?
C2 H2a 0.9800 . ?
C2 H2b 0.9800 . ?
C2 H2c 0.9800 . ?

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
C1 O3 C4 121.41(14) . . ?
B10 O1 C4 111.40(14) . . ?
O1 C4 O3 122.99(16) . . ?
N1 C4 O3 119.34(16) . . ?
N1 C4 O1 117.66(16) . . ?
C6 C5 H5 108.78(11) . . ?
B10 C5 H5 108.78(10) . . ?
B10 C5 C6 109.50(16) . . ?
C11 C5 H5 108.78(11) . . ?
C11 C5 C6 113.80(16) . . ?
C11 C5 B10 107.09(16) . . ?
H6a C6 C5 108.36(10) . . ?
H6b C6 C5 108.36(10) . . ?
H6b C6 H6a 107.4 . . ?
C13 C6 C5 115.70(17) . . ?
C13 C6 H6a 108.36(11) . . ?
C13 C6 H6b 108.36(12) . . ?
C8 C7 H7 108.48(11) . . ?
B10 C7 H7 108.48(10) . . ?
B10 C7 C8 110.08(16) . . ?
C12 C7 H7 108.48(11) . . ?
C12 C7 C8 113.75(17) . . ?
C12 C7 B10 107.45(17) . . ?
H8a C8 C7 108.37(11) . . ?
H8b C8 C7 108.37(10) . . ?
H8b C8 H8a 107.4 . . ?
C13 C8 C7 115.62(17) . . ?
C13 C8 H8a 108.37(12) . . ?
C13 C8 H8b 108.37(11) . . ?
C5 B10 O1 110.19(15) . . ?
C7 B10 O1 110.30(15) . . ?
C7 B10 C5 108.70(15) . . ?
N1 B10 O1 94.01(13) 7_565 . ?
N1 B10 C5 116.80(16) 7_565 . ?
N1 B10 C7 115.88(16) 7_565 . ?
H11a C11 C5 108.57(11) . . ?
H11b C11 C5 108.57(11) . . ?
H11b C11 H11a 107.5 . . ?
C14 C11 C5 114.78(18) . . ?
C14 C11 H11a 108.57(13) . . ?
C14 C11 H11b 108.57(12) . . ?
H12a C12 C7 108.65(12) . . ?
H12b C12 C7 108.65(11) . . ?
H12b C12 H12a 107.6 . . ?
C14 C12 C7 114.45(18) . . ?
C14 C12 H12a 108.65(12) . . ?
C14 C12 H12b 108.65(13) . . ?
C8 C13 C6 115.33(17) . . ?
H13a C13 C6 108.44(12) . . ?
H13a C13 C8 108.44(12) . . ?
H13b C13 C6 108.44(11) . . ?
H13b C13 C8 108.44(12) . . ?
H13b C13 H13a 107.5 . . ?
C12 C14 C11 113.87(18) . . ?
H14a C14 C11 108.78(12) . . ?
H14a C14 C12 108.78(12) . . ?
H14b C14 C11 108.78(13) . . ?
H14b C14 C12 108.78(13) . . ?
H14b C14 H14a 107.7 . . ?
B10 N1 C4 143.07(15) 7_565 . ?
N1 N1 C4 107.10(17) 7_565 . ?
N1 N1 B10 109.82(17) 7_565 7_565 ?
C9 C1 O3 101.32(15) . . ?
C3 C1 O3 109.19(17) . . ?
C3 C1 C9 110.89(19) . . ?
C2 C1 O3 110.10(16) . . ?
C2 C1 C9 111.41(19) . . ?
C2 C1 C3 113.3(2) . . ?
H9a C9 C1 109.5 . . ?
H9b C9 C1 109.5 . . ?
H9b C9 H9a 109.5 . . ?
H9c C9 C1 109.5 . . ?
H9c C9 H9a 109.5 . . ?
H9c C9 H9b 109.5 . . ?
H3a C3 C1 109.5 . . ?
H3b C3 C1 109.5 . . ?
H3b C3 H3a 109.5 . . ?
H3c C3 C1 109.5 . . ?
H3c C3 H3a 109.5 . . ?
H3c C3 H3b 109.5 . . ?
H2a C2 C1 109.5 . . ?
H2b C2 C1 109.5 . . ?
H2b C2 H2a 109.5 . . ?
H2c C2 C1 109.5 . . ?
H2c C2 H2a 109.5 . . ?
H2c C2 H2b 109.5 . . ?

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
O3 C4 O1 B10 -178.41(18) . . . . ?
O3 C4 N1 B10 -0.5(3) . . . 7_565 ?
O3 C4 N1 N1 178.0(2) . . . 7_565 ?
O1 C4 N1 B10 -179.46(16) . . . 7_565 ?
O1 C4 N1 N1 -0.90(19) . . . 7_565 ?
O1 B10 C5 C6 179.26(15) . . . . ?
O1 B10 C5 C11 -56.92(16) . . . . ?
O1 B10 C7 C8 -179.50(15) . . . . ?
O1 B10 C7 C12 56.13(17) . . . . ?
O1 B10 N1 C4 -179.15(15) . . 7_565 7_565 ?
O1 B10 N1 N1 -0.61(17) . . 7_565 . ?
C4 N1 B10 C5 64.1(3) . . 7_565 7_565 ?
C4 N1 B10 C7 -66.0(3) . . 7_565 7_565 ?
C4 N1 N1 C4 180.0(2) . . 7_565 7_565 ?
C4 N1 N1 B10 0.92(16) . . 7_565 . ?
C5 C6 C13 C8 -41.2(2) . . . . ?
C5 B10 C7 C8 59.58(17) . . . . ?
C5 B10 C7 C12 -64.78(17) . . . . ?
C5 B10 N1 N1 114.42(19) . . 7_565 . ?
C5 C11 C14 C12 45.0(2) . . . . ?
C6 C13 C8 C7 40.7(2) . . . . ?
C7 B10 N1 N1 -115.48(19) . . 7_565 . ?
C7 C12 C14 C11 -45.3(2) . . . . ?
B10 N1 N1 B10 180.0(2) . 7_565 . 7_565 ?


_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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2302182'
loop_
_audit_author_name
_audit_author_address
'Douglas Stephan'
;University of Toronto
Canada
;
_audit_update_record             
;
2023-10-19 deposited with the CCDC.	2023-11-30 downloaded from the CCDC.
;
_audit_creation_date             2023-09-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'C8 H21 N2, B F4.25'
_chemical_formula_sum            'C8 H21 B F4.25 N2'
_chemical_formula_weight         236.837
_chemical_absolute_configuration unk
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
B 0.00156 0.00068 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.19320 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
F 0.01756 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           ' P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   8.750(2)
_cell_length_b                   8.991(3)
_cell_length_c                   15.956(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1255.3(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6449
_cell_measurement_temperature    149.68
_cell_measurement_theta_max      22.43
_cell_measurement_theta_min      2.55
_exptl_crystal_description       block
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      .
_exptl_crystal_F_000             505.472
_diffrn_reflns_av_R_equivalents  0.1253
_diffrn_reflns_av_unetI/netI     0.0698
_diffrn_reflns_Laue_measured_fraction_full 0.9961
_diffrn_reflns_Laue_measured_fraction_max 0.9961
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29745
_diffrn_reflns_point_group_measured_fraction_full 0.9973
_diffrn_reflns_point_group_measured_fraction_max 0.9973
_diffrn_reflns_theta_full        24.9961
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.55
_diffrn_ambient_temperature      149.68
_diffrn_measured_fraction_theta_full 0.9961
_diffrn_measured_fraction_theta_max 0.9961
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.999
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              18
_reflns_limit_l_min              -18
_reflns_number_gt                1836
_reflns_number_total             2205
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.7243
_refine_diff_density_min         -0.3960
_refine_diff_density_rms         0.0844
_refine_ls_abs_structure_details 
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.2(6)
_refine_ls_d_res_high            0.8410
_refine_ls_d_res_low             7.9780
_refine_ls_extinction_coef       0.006(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0762
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0744
_refine_ls_restrained_S_all      1.0762
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1242P)²+1.2125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1971
_refine_ls_wR_factor_ref         0.2216
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: F6(0.25)
3.a Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c), C17(H17a,H17b,H17c), C21(H21a,H21b,H21c), C20(H20a,H20b,
 H20c), C19(H19a,H19b,H19c), C22(H22a,H22b,H22c)
;
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_group
N1 N -0.3414(4) -0.0603(4) 0.1195(2) 0.0311(8) Uani 1.000000 . . .
C10 C -0.2914(4) 0.0784(4) 0.0747(2) 0.0281(8) Uani 1.000000 . . .
N2 N -0.2319(4) -0.1796(4) 0.1114(2) 0.0288(8) Uani 1.000000 . . .
C11 C -0.2445(4) -0.2960(4) 0.1815(2) 0.0279(9) Uani 1.000000 . . .
C18 C -0.2446(6) 0.0513(5) -0.0157(3) 0.0419(11) Uani 1.000000 . . .
H18a H -0.155(2) -0.014(3) -0.0170(3) 0.0629(17) Uiso 1.000000 GR . .
H18b H -0.3290(16) 0.004(4) -0.0458(6) 0.0629(17) Uiso 1.000000 GR . .
H18c H -0.220(4) 0.1464(6) -0.0424(7) 0.0629(17) Uiso 1.000000 GR . .
B9 B -0.7963(5) -0.1050(5) 0.0819(3) 0.0313(10) Uani 1.000000 . . .
C17 C -0.1629(6) 0.1494(5) 0.1248(3) 0.0430(11) Uani 1.000000 . . .
H17a H -0.1929(17) 0.156(3) 0.1839(5) 0.0646(17) Uiso 1.000000 GR . .
H17b H -0.0705(12) 0.089(2) 0.1198(18) 0.0646(17) Uiso 1.000000 GR . .
H17c H -0.143(3) 0.2493(16) 0.1030(14) 0.0646(17) Uiso 1.000000 GR . .
C21 C -0.2086(5) -0.2169(5) 0.2629(2) 0.0377(10) Uani 1.000000 . . .
H21a H -0.284(2) -0.138(2) 0.2725(10) 0.0565(15) Uiso 1.000000 GR . .
H21b H -0.212(4) -0.2883(9) 0.3093(4) 0.0565(15) Uiso 1.000000 GR . .
H21c H -0.1063(16) -0.173(3) 0.2596(8) 0.0565(15) Uiso 1.000000 GR . .
C20 C -0.1230(6) -0.4128(5) 0.1611(3) 0.0465(12) Uani 1.000000 . . .
H20a H -0.123(3) -0.490(2) 0.2044(12) 0.0698(18) Uiso 1.000000 GR . .
H20b H -0.146(2) -0.458(3) 0.1065(11) 0.0698(18) Uiso 1.000000 GR . .
H20c H -0.0222(8) -0.3654(9) 0.159(2) 0.0698(18) Uiso 1.000000 GR . .
C19 C -0.4329(5) 0.1778(6) 0.0787(4) 0.0521(14) Uani 1.000000 . . .
H19a H -0.5195(12) 0.1265(18) 0.053(2) 0.078(2) Uiso 1.000000 GR . .
H19b H -0.457(3) 0.200(3) 0.1374(4) 0.078(2) Uiso 1.000000 GR . .
H19c H -0.4128(16) 0.2709(19) 0.049(2) 0.078(2) Uiso 1.000000 GR . .
C22 C -0.4028(6) -0.3601(5) 0.1805(4) 0.0500(13) Uani 1.000000 . . .
H22a H -0.4100(13) -0.440(3) 0.2221(17) 0.075(2) Uiso 1.000000 GR . .
H22b H -0.4769(7) -0.2820(11) 0.194(2) 0.075(2) Uiso 1.000000 GR . .
H22c H -0.4248(17) -0.400(4) 0.1247(8) 0.075(2) Uiso 1.000000 GR . .
F2 F -0.7934(10) 0.0397(9) 0.0566(6) 0.125(3) Uani 1.000000 . . 2
F5 F -0.6639(3) -0.1725(4) 0.0550(2) 0.0679(10) Uani 1.000000 . . 2
F7 F -0.9129(3) -0.1768(4) 0.0386(2) 0.0690(10) Uani 1.000000 . . 2
F3 F -0.8281(10) -0.1175(5) 0.1627(2) 0.148(3) Uani 1.000000 . . 1
F6 F -0.7956(10) 0.0452(8) 0.0568(7) 0.006(2) Uani 0.250000 . P 1
H2a H -0.139(4) -0.135(4) 0.115(2) 0.010(8) Uiso 1.000000 . . .
H1 H -0.417(6) -0.094(6) 0.096(3) 0.035(13) Uiso 1.000000 . . .
H2b H -0.253(7) -0.220(7) 0.070(4) 0.069(19) 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
N1 C10 1.502(5) . ?
N1 N2 1.443(5) . ?
N1 H1 0.82(5) . ?
C10 C18 1.519(6) . ?
C10 C17 1.519(6) . ?
C10 C19 1.529(6) . ?
N2 C11 1.535(4) . ?
N2 H2a 0.91(4) . ?
N2 H2b 0.77(7) . ?
C11 C21 1.514(5) . ?
C11 C20 1.529(6) . ?
C11 C22 1.500(6) . ?
C18 H18a 0.9800 . ?
C18 H18b 0.9800 . ?
C18 H18c 0.9800 . ?
B9 F2 1.362(9) . ?
B9 F5 1.377(5) . ?
B9 F7 1.391(5) . ?
B9 F3 1.325(6) . ?
B9 F6 1.408(8) . ?
C17 H17a 0.9800 . ?
C17 H17b 0.9800 . ?
C17 H17c 0.9800 . ?
C21 H21a 0.9800 . ?
C21 H21b 0.9800 . ?
C21 H21c 0.9800 . ?
C20 H20a 0.9800 . ?
C20 H20b 0.9800 . ?
C20 H20c 0.9800 . ?
C19 H19a 0.9800 . ?
C19 H19b 0.9800 . ?
C19 H19c 0.9800 . ?
C22 H22a 0.9800 . ?
C22 H22b 0.9800 . ?
C22 H22c 0.9800 . ?

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
N2 N1 C10 112.4(3) . . ?
H1 N1 C10 109(4) . . ?
H1 N1 N2 103(4) . . ?
C18 C10 N1 113.4(3) . . ?
C17 C10 N1 108.4(3) . . ?
C17 C10 C18 111.5(3) . . ?
C19 C10 N1 103.3(3) . . ?
C19 C10 C18 110.6(3) . . ?
C19 C10 C17 109.4(4) . . ?
C11 N2 N1 113.2(3) . . ?
H2a N2 N1 105(2) . . ?
H2a N2 C11 108(2) . . ?
H2b N2 N1 105(5) . . ?
H2b N2 C11 106(5) . . ?
H2b N2 H2a 119(5) . . ?
C21 C11 N2 106.8(3) . . ?
C20 C11 N2 105.3(3) . . ?
C20 C11 C21 111.2(3) . . ?
C22 C11 N2 108.7(3) . . ?
C22 C11 C21 112.4(4) . . ?
C22 C11 C20 112.1(4) . . ?
H18a C18 C10 109.5 . . ?
H18b C18 C10 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 C10 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
F5 B9 F2 108.3(5) . . ?
F7 B9 F2 108.1(6) . . ?
F7 B9 F5 104.9(3) . . ?
F3 B9 F2 112.0(6) . . ?
F3 B9 F5 116.2(5) . . ?
F3 B9 F7 106.8(5) . . ?
F6 B9 F2 1.1(7) . . ?
F6 B9 F5 109.3(5) . . ?
F6 B9 F7 107.9(5) . . ?
F6 B9 F3 111.1(6) . . ?
H17a C17 C10 109.5 . . ?
H17b C17 C10 109.5 . . ?
H17b C17 H17a 109.5 . . ?
H17c C17 C10 109.5 . . ?
H17c C17 H17a 109.5 . . ?
H17c C17 H17b 109.5 . . ?
H21a C21 C11 109.5 . . ?
H21b C21 C11 109.5 . . ?
H21b C21 H21a 109.5 . . ?
H21c C21 C11 109.5 . . ?
H21c C21 H21a 109.5 . . ?
H21c C21 H21b 109.5 . . ?
H20a C20 C11 109.5 . . ?
H20b C20 C11 109.5 . . ?
H20b C20 H20a 109.5 . . ?
H20c C20 C11 109.5 . . ?
H20c C20 H20a 109.5 . . ?
H20c C20 H20b 109.5 . . ?
H19a C19 C10 109.5 . . ?
H19b C19 C10 109.5 . . ?
H19b C19 H19a 109.5 . . ?
H19c C19 C10 109.5 . . ?
H19c C19 H19a 109.5 . . ?
H19c C19 H19b 109.5 . . ?
H22a C22 C11 109.5 . . ?
H22b C22 C11 109.5 . . ?
H22b C22 H22a 109.5 . . ?
H22c C22 C11 109.5 . . ?
H22c C22 H22a 109.5 . . ?
H22c C22 H22b 109.5 . . ?

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
N1 N2 C11 C21 -62.8(4) . . . . ?
N1 N2 C11 C20 178.9(4) . . . . ?
N1 N2 C11 C22 58.6(4) . . . . ?


_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_2
_database_code_depnum_ccdc_archive 'CCDC 2302183'
loop_
_audit_author_name
_audit_author_address
'Douglas Stephan'
;University of Toronto
Canada
;
_audit_update_record             
;
2023-10-19 deposited with the CCDC.	2023-11-30 downloaded from the CCDC.
;
_audit_creation_date             2023-09-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'B0.5 C12 F10, C4 H9.5 N'
_chemical_formula_sum            'C16 H9.5 B0.5 F10 N'
_chemical_formula_weight         411.157
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
B 0.00156 0.00068 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.19320 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
F 0.01756 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   20.394(3)
_cell_length_b                   8.2279(11)
_cell_length_c                   19.557(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.375(6)
_cell_angle_gamma                90
_cell_volume                     3267.2(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3733
_cell_measurement_temperature    150.02
_cell_measurement_theta_max      21.96
_cell_measurement_theta_min      2.76
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_density_meas      .
_exptl_crystal_description       Block
_exptl_crystal_F_000             1641.935
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_Laue_measured_fraction_full 0.9997
_diffrn_reflns_Laue_measured_fraction_max 0.9997
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            32500
_diffrn_reflns_point_group_measured_fraction_full 0.9997
_diffrn_reflns_point_group_measured_fraction_max 0.9997
_diffrn_reflns_theta_full        24.9934
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.01
_diffrn_ambient_temperature      150.02
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              24
_reflns_limit_h_min              -24
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                1869
_reflns_number_total             2869
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.4123
_refine_diff_density_min         -0.3941
_refine_diff_density_rms         0.1030
_refine_ls_d_res_high            0.8411
_refine_ls_d_res_low             10.1524
_refine_ls_goodness_of_fit_ref   1.0887
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    14
_refine_ls_number_parameters     252
_refine_ls_number_reflns         2869
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.0887
_refine_ls_shift/su_max          -0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0354P)²+3.1341P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0992
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H1(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1)
3.b Idealised Me refined as rotating group:
 C26(H26a,H26b,H26c), C27(H27a,H27b,H27c), C28(H28a,H28b,H28c)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
F1 F 0.34869(7) 0.94643(18) 0.23178(7) 0.0351(4) Uani 1.000000 1 . . .
F2 F 0.55454(7) 0.78118(18) 0.15954(7) 0.0331(4) Uani 1.000000 1 . . .
F3 F 0.28936(7) 0.72398(18) 0.15153(8) 0.0391(4) Uani 1.000000 1 . . .
F4 F 0.50277(7) 1.07256(18) 0.09476(7) 0.0357(4) Uani 1.000000 1 . . .
F5 F 0.49306(8) 0.55242(18) 0.08134(8) 0.0401(4) Uani 1.000000 1 . . .
F6 F 0.57781(9) 1.28760(19) 0.03925(8) 0.0486(5) Uani 1.000000 1 . . .
F7 F 0.59600(8) 1.23040(18) 0.31612(7) 0.0386(4) Uani 1.000000 1 . . .
F8 F 0.67276(9) 1.4429(2) 0.25838(9) 0.0537(5) Uani 1.000000 1 . . .
F9 F 0.35936(8) 0.52000(18) 0.07594(8) 0.0427(4) Uani 1.000000 1 . . .
F10 F 0.66506(9) 1.47476(19) 0.11867(10) 0.0571(5) Uani 1.000000 1 . . .
N1 N 0.72750(10) 1.7410(3) 0.01797(11) 0.0328(6) Uani 1.000000 1 . . .
H1 H 0.72092(10) 1.6449(3) 0.03587(11) 0.0394(7) Uiso 0.500000 1 R . P
C12 C 0.48768(12) 0.7719(3) 0.15901(13) 0.0263(6) Uani 1.000000 1 . . .
C13 C 0.38816(13) 0.8563(3) 0.19431(13) 0.0261(6) Uani 1.000000 1 . . .
C14 C 0.45566(12) 0.8821(3) 0.19865(12) 0.0227(6) Uani 1.000000 1 . . .
C15 C 0.39047(14) 0.6358(3) 0.11554(13) 0.0287(6) Uani 1.000000 1 . . .
C16 C 0.54630(13) 1.1349(3) 0.20915(13) 0.0254(6) Uani 1.000000 1 . . .
C17 C 0.45781(13) 0.6523(3) 0.11822(13) 0.0278(6) Uani 1.000000 1 . . .
C18 C 0.62647(15) 1.3664(3) 0.14804(16) 0.0380(8) Uani 1.000000 1 . . .
C19 C 0.58298(14) 1.2722(3) 0.10824(14) 0.0336(7) Uani 1.000000 1 . . .
C20 C 0.59018(13) 1.2393(3) 0.24640(13) 0.0306(7) Uani 1.000000 1 . . .
C21 C 0.54448(13) 1.1602(3) 0.13903(14) 0.0283(6) Uani 1.000000 1 . . .
B22 B 0.5 1.0094(5) 0.25 0.0231(9) Uani 1.000000 2 S T P
C23 C 0.35574(13) 0.7387(3) 0.15386(13) 0.0278(6) Uani 1.000000 1 . . .
C2 C 0.68321(13) 1.8790(3) 0.03227(14) 0.0328(7) Uani 1.000000 1 . . .
C25 C 0.63016(14) 1.3512(3) 0.21825(15) 0.0361(7) Uani 1.000000 1 . . .
C26 C 0.61431(14) 1.8174(4) 0.00935(16) 0.0501(9) Uani 1.000000 1 . . .
H26a H 0.6098(4) 1.803(2) -0.04060(19) 0.0752(13) Uiso 1.000000 1 GR . .
H26b H 0.6071(4) 1.7132(13) 0.0317(8) 0.0752(13) Uiso 1.000000 1 GR . .
H26c H 0.58170(15) 1.8966(12) 0.0221(9) 0.0752(13) Uiso 1.000000 1 GR . .
C27 C 0.69347(14) 1.8969(3) 0.11019(14) 0.0351(7) Uani 1.000000 1 . . .
H27a H 0.6835(8) 1.7935(7) 0.13184(14) 0.0527(11) Uiso 1.000000 1 GR . .
H27b H 0.7393(2) 1.927(2) 0.12378(16) 0.0527(11) Uiso 1.000000 1 GR . .
H27c H 0.6642(6) 1.9817(15) 0.12500(17) 0.0527(11) Uiso 1.000000 1 GR . .
C28 C 0.70108(17) 2.0325(4) -0.00477(17) 0.0551(10) Uani 1.000000 1 . . .
H28a H 0.7466(4) 2.0630(15) 0.0102(8) 0.0826(14) Uiso 1.000000 1 GR . .
H28b H 0.6968(10) 2.0129(8) -0.05442(18) 0.0826(14) Uiso 1.000000 1 GR . .
H28c H 0.6714(7) 2.1207(8) 0.0059(9) 0.0826(14) Uiso 1.000000 1 GR . .


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 C13 1.358(3) . ?
F2 C12 1.365(3) . ?
F3 C23 1.356(3) . ?
F4 C21 1.362(3) . ?
F5 C17 1.345(3) . ?
F6 C19 1.349(3) . ?
F7 C20 1.360(3) . ?
F8 C25 1.346(3) . ?
F9 C15 1.348(3) . ?
F10 C18 1.352(3) . ?
N1 N1 1.216(4) 7_685 ?
N1 H1 0.8800 . ?
N1 C2 1.494(3) . ?
C12 C14 1.395(3) . ?
C12 C17 1.373(4) . ?
C13 C14 1.388(3) . ?
C13 C23 1.379(4) . ?
C14 B22 1.659(4) 2_655 ?
C15 C17 1.376(4) . ?
C15 C23 1.371(4) . ?
C16 C20 1.395(4) . ?
C16 C21 1.384(4) . ?
C16 B22 1.655(4) 2_655 ?
C18 C19 1.366(4) . ?
C18 C25 1.374(4) . ?
C19 C21 1.384(4) . ?
C20 C25 1.378(4) . ?
C2 C26 1.521(4) . ?
C2 C27 1.526(4) . ?
C2 C28 1.517(4) . ?
C26 H26a 0.9800 . ?
C26 H26b 0.9800 . ?
C26 H26c 0.9800 . ?
C27 H27a 0.9800 . ?
C27 H27b 0.9800 . ?
C27 H27c 0.9800 . ?
C28 H28a 0.9800 . ?
C28 H28b 0.9800 . ?
C28 H28c 0.9800 . ?

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
C2 N1 H1 119.43(13) . . ?
C14 C12 F2 118.6(2) . . ?
C17 C12 F2 115.7(2) . . ?
C17 C12 C14 125.7(2) . . ?
C14 C13 F1 121.2(2) . . ?
C23 C13 F1 114.6(2) . . ?
C23 C13 C14 124.2(2) . . ?
C13 C14 C12 112.3(2) . . ?
B22 C14 C12 119.3(2) 2_655 . ?
B22 C14 C13 128.0(2) 2_655 . ?
C17 C15 F9 120.4(2) . . ?
C23 C15 F9 120.7(2) . . ?
C23 C15 C17 118.9(2) . . ?
C21 C16 C20 112.4(2) . . ?
B22 C16 C20 119.9(2) 2_655 . ?
B22 C16 C21 127.5(2) 2_655 . ?
C12 C17 F5 121.3(2) . . ?
C15 C17 F5 120.0(2) . . ?
C15 C17 C12 118.7(2) . . ?
C19 C18 F10 120.3(3) . . ?
C25 C18 F10 120.3(3) . . ?
C25 C18 C19 119.3(3) . . ?
C18 C19 F6 120.1(3) . . ?
C21 C19 F6 120.2(3) . . ?
C21 C19 C18 119.7(2) . . ?
C16 C20 F7 118.8(2) . . ?
C25 C20 F7 115.9(2) . . ?
C25 C20 C16 125.2(2) . . ?
C16 C21 F4 120.5(2) . . ?
C19 C21 F4 114.9(2) . . ?
C19 C21 C16 124.5(3) . . ?
C14 B22 C14 101.7(3) 2_655 . ?
C16 B22 C14 113.90(12) . . ?
C16 B22 C14 112.51(12) . 2_655 ?
C16 B22 C14 112.51(12) 2_655 . ?
C16 B22 C14 113.90(12) 2_655 2_655 ?
C16 B22 C16 102.7(3) . 2_655 ?
C13 C23 F3 120.4(2) . . ?
C15 C23 F3 119.5(2) . . ?
C15 C23 C13 120.2(2) . . ?
C26 C2 N1 104.4(2) . . ?
C27 C2 N1 103.4(2) . . ?
C27 C2 C26 111.3(2) . . ?
C28 C2 N1 111.5(2) . . ?
C28 C2 C26 113.2(3) . . ?
C28 C2 C27 112.3(2) . . ?
C18 C25 F8 120.2(3) . . ?
C20 C25 F8 121.0(3) . . ?
C20 C25 C18 118.8(3) . . ?
H26a C26 C2 109.5 . . ?
H26b C26 C2 109.5 . . ?
H26b C26 H26a 109.5 . . ?
H26c C26 C2 109.5 . . ?
H26c C26 H26a 109.5 . . ?
H26c C26 H26b 109.5 . . ?
H27a C27 C2 109.5 . . ?
H27b C27 C2 109.5 . . ?
H27b C27 H27a 109.5 . . ?
H27c C27 C2 109.5 . . ?
H27c C27 H27a 109.5 . . ?
H27c C27 H27b 109.5 . . ?
H28a C28 C2 109.5 . . ?
H28b C28 C2 109.5 . . ?
H28b C28 H28a 109.5 . . ?
H28c C28 C2 109.5 . . ?
H28c C28 H28a 109.5 . . ?
H28c C28 H28b 109.5 . . ?

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 C13 C14 C12 176.9(2) . . . . ?
F1 C13 C14 B22 4.2(3) . . . 2_655 ?
F1 C13 C23 F3 2.5(2) . . . . ?
F1 C13 C23 C15 -177.6(2) . . . . ?
F2 C12 C14 C13 -178.7(2) . . . . ?
F2 C12 C14 B22 -5.3(3) . . . 2_655 ?
F2 C12 C17 F5 -0.3(2) . . . . ?
F2 C12 C17 C15 179.7(2) . . . . ?
F3 C23 C13 C14 -178.6(2) . . . . ?
F3 C23 C15 F9 -0.3(3) . . . . ?
F3 C23 C15 C17 179.8(2) . . . . ?
F4 C21 C16 C20 -177.9(2) . . . . ?
F4 C21 C16 B22 -2.5(3) . . . 2_655 ?
F4 C21 C19 F6 -0.4(2) . . . . ?
F4 C21 C19 C18 180.0(2) . . . . ?
F5 C17 C12 C14 179.4(2) . . . . ?
F5 C17 C15 F9 -0.2(3) . . . . ?
F5 C17 C15 C23 179.7(2) . . . . ?
F6 C19 C18 F10 -0.6(3) . . . . ?
F6 C19 C18 C25 178.8(2) . . . . ?
F6 C19 C21 C16 179.8(2) . . . . ?
F7 C20 C16 C21 178.6(2) . . . . ?
F7 C20 C16 B22 2.8(3) . . . 2_655 ?
F7 C20 C25 F8 1.0(3) . . . . ?
F7 C20 C25 C18 -179.8(2) . . . . ?
F8 C25 C18 F10 -0.7(3) . . . . ?
F8 C25 C18 C19 179.9(2) . . . . ?
F8 C25 C20 C16 -177.6(2) . . . . ?
F9 C15 C17 C12 179.8(2) . . . . ?
F9 C15 C23 C13 179.8(2) . . . . ?
F10 C18 C19 C21 179.1(2) . . . . ?
F10 C18 C25 C20 -179.9(2) . . . . ?
N1 N1 C2 C26 124.3(3) 7_685 . . . ?
N1 N1 C2 C27 -119.1(3) 7_685 . . . ?
N1 N1 C2 C28 1.8(4) 7_685 . . . ?
C12 C14 C13 C23 -1.9(3) . . . . ?
C12 C14 B22 C14 -59.7(3) . . 2_655 2_655 ?
C12 C14 B22 C16 61.6(2) . . 2_655 . ?
C12 C14 B22 C16 178.0(2) . . 2_655 2_655 ?
C12 C17 C15 C23 -0.3(3) . . . . ?
C13 C14 B22 C14 112.6(2) . . 2_655 2_655 ?
C13 C14 B22 C16 -126.1(3) . . 2_655 . ?
C13 C14 B22 C16 -9.7(3) . . 2_655 2_655 ?
C13 C23 C15 C17 -0.1(3) . . . . ?
C14 B22 C16 C20 -59.6(3) 2_655 . . . ?
C14 B22 C16 C20 -174.7(2) . 2_655 . . ?
C14 B22 C16 C21 125.33(19) 2_655 . . . ?
C14 B22 C16 C21 10.2(3) . 2_655 . . ?
C16 C20 C25 C18 1.6(3) . . . . ?
C16 C21 C19 C18 0.1(3) . . . . ?
C16 B22 C16 C20 63.33(18) 2_655 . . . ?
C16 B22 C16 C21 -111.76(17) 2_655 . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
