# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_20210423bl_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2171509'
loop_
_audit_author_name
_audit_author_address
'Jian-Bo Xie'
;Northwest Agriculture and Forestry University
China
;
_audit_update_record             
;
2022-05-09 deposited with the CCDC.	2022-11-25 downloaded from the CCDC.
;
_audit_creation_date             2021-04-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H29 B F N O3'
_chemical_formula_sum            'C23 H29 B F N O3'
_chemical_formula_weight         397.28
_chemical_absolute_configuration ad
_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 0.0148 0.0070 '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 0.0073 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0599 0.0411 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.0208(5)
_cell_length_b                   9.4096(5)
_cell_length_c                   12.1630(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.034(2)
_cell_angle_gamma                90
_cell_volume                     1145.26(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9726
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      53.96
_cell_measurement_theta_min      5.104
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.416
_exptl_absorpt_correction_T_max  0.7506
_exptl_absorpt_correction_T_min  0.5772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1505 before and 0.0714 after correction. The Ratio of minimum to maximum transmission is 0.7690. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            36956
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.101
_diffrn_reflns_theta_min         5.110
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                3897
_reflns_number_total             4152
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 1653 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4152
_refine_ls_number_restraints     100
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0577
_refine_ls_restrained_S_all      1.139
_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)+(0.1135P)²+0.3158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1624
_refine_ls_wR_factor_ref         0.1659
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 B1, O2, O3, C21, C22, C21A, C22A, C23, C24, C25, C24A, C25A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
B1 \\sim O2 \\sim O3 \\sim C21 \\sim C22 \\sim C21A \\sim C22A \\sim C23 \\sim
C24 \\sim C25 \\sim C24A \\sim C25A: within 2A with sigma of 0.005 and sigma
for terminal atoms of 0.01
Uanis(C21) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=
 Sof(C24A)=Sof(H24D)=Sof(H24E)=Sof(H24F)=Sof(C25A)=Sof(H25D)=Sof(H25E)=
 Sof(H25F)=1-FVAR(1)
 Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(C22A)=Sof(H22D)=Sof(H22E)=
 Sof(H22F)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(C25)=Sof(H25A)=Sof(H25B)=
 Sof(H25C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C3(H3), C13(H13)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
5.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16),
 C17(H17), C18(H18)
5.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C21A(H21D,H21E,
 H21F), C22A(H22D,H22E,H22F), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C),
 C24A(H24D,H24E,H24F), C25A(H25D,H25E,H25F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.3030(2) 0.7602(3) 0.7082(2) 0.0657(7) Uani 1 1 d . . . . .
O1 O 0.4835(3) 0.7004(2) 0.4848(2) 0.0391(6) Uani 1 1 d . . . . .
N2 N 0.4818(3) 0.4753(3) 0.4218(2) 0.0309(6) Uani 1 1 d . . . . .
H2 H 0.502714 0.386074 0.435997 0.037 Uiso 1 1 calc R . . . .
C1 C 0.4130(3) 0.5099(3) 0.3163(2) 0.0351(7) Uani 1 1 d . . . . .
H1A H 0.447110 0.447106 0.258824 0.042 Uiso 1 1 calc R . . . .
H1B H 0.434565 0.609034 0.296698 0.042 Uiso 1 1 calc R . . . .
C2 C 0.5139(3) 0.5736(3) 0.4971(2) 0.0281(6) Uani 1 1 d . . . . .
C3 C 0.5947(3) 0.5227(3) 0.5992(2) 0.0314(7) Uani 1 1 d . . . . .
H3 H 0.597508 0.416485 0.599058 0.038 Uiso 1 1 calc R . . . .
C4 C 0.7368(3) 0.5801(4) 0.5939(3) 0.0442(8) Uani 1 1 d . . . . .
H4A H 0.777437 0.542093 0.528467 0.066 Uiso 1 1 calc GR . . . .
H4B H 0.789930 0.550886 0.660007 0.066 Uiso 1 1 calc GR . . . .
H4C H 0.734304 0.684066 0.589744 0.066 Uiso 1 1 calc GR . . . .
C7 C 0.2626(3) 0.4941(4) 0.3163(3) 0.0394(8) Uani 1 1 d . . . . .
C8 C 0.1944(4) 0.4141(4) 0.2357(3) 0.0524(10) Uani 1 1 d . . . . .
H8 H 0.241400 0.367407 0.180331 0.063 Uiso 1 1 calc R . . . .
C9 C 0.0547(5) 0.4033(5) 0.2372(4) 0.0652(13) Uani 1 1 d . . . . .
H9 H 0.007883 0.348647 0.182014 0.078 Uiso 1 1 calc R . . . .
C10 C -0.0149(5) 0.4683(6) 0.3149(5) 0.0710(14) Uani 1 1 d . . . . .
H10 H -0.109147 0.457961 0.315615 0.085 Uiso 1 1 calc R . . . .
C11 C 0.0535(5) 0.5498(8) 0.3931(5) 0.0760(15) Uani 1 1 d . . . . .
H11 H 0.005632 0.598245 0.447094 0.091 Uiso 1 1 calc R . . . .
C12 C 0.1900(4) 0.5620(6) 0.3939(4) 0.0597(12) Uani 1 1 d . . . . .
H12 H 0.235273 0.618218 0.448936 0.072 Uiso 1 1 calc R . . . .
C13 C 0.5280(3) 0.5741(3) 0.7039(2) 0.0338(7) Uani 1 1 d . . . . .
H13 H 0.528437 0.680409 0.704060 0.041 Uiso 1 1 calc R . . . .
C14 C 0.3840(3) 0.5244(4) 0.7031(2) 0.0347(7) Uani 1 1 d . . . . .
C15 C 0.3512(4) 0.3813(4) 0.6984(3) 0.0472(8) Uani 1 1 d . . . . .
H15 H 0.421201 0.313085 0.700583 0.057 Uiso 1 1 calc R . . . .
C16 C 0.2194(4) 0.3340(5) 0.6907(4) 0.0565(10) Uani 1 1 d . . . . .
H16 H 0.200263 0.235244 0.686604 0.068 Uiso 1 1 calc R . . . .
C17 C 0.1162(4) 0.4327(6) 0.6891(4) 0.0613(11) Uani 1 1 d . . . . .
H17 H 0.025922 0.401701 0.682791 0.074 Uiso 1 1 calc R . . . .
C18 C 0.1448(4) 0.5743(6) 0.6965(4) 0.0613(11) Uani 1 1 d . . . . .
H18 H 0.074910 0.642341 0.697560 0.074 Uiso 1 1 calc R . . . .
C19 C 0.2770(4) 0.6174(4) 0.7025(3) 0.0455(8) Uani 1 1 d . . . . .
C20 C 0.7189(7) 0.5244(6) 0.9797(4) 0.0802(17) Uani 1 1 d . . . . .
B1 B 0.6079(4) 0.5209(4) 0.8116(3) 0.0400(8) Uani 1 1 d . U . . .
O2 O 0.6379(4) 0.6050(4) 0.8974(2) 0.0643(8) Uani 1 1 d . U . . .
O3 O 0.6535(4) 0.3881(4) 0.8265(3) 0.0759(10) Uani 1 1 d . U . . .
C21 C 0.8677(16) 0.581(2) 0.9575(16) 0.100(5) Uani 0.433(8) 1 d . U P A 2
H21A H 0.862889 0.679639 0.932193 0.150 Uiso 0.433(8) 1 calc GR . P A 2
H21B H 0.906374 0.521671 0.900970 0.150 Uiso 0.433(8) 1 calc GR . P A 2
H21C H 0.923832 0.575202 1.025789 0.150 Uiso 0.433(8) 1 calc GR . P A 2
C22 C 0.711(2) 0.563(2) 1.0876(11) 0.095(4) Uani 0.433(8) 1 d . U P A 2
H22A H 0.771394 0.643478 1.103805 0.143 Uiso 0.433(8) 1 calc GR . P A 2
H22B H 0.737567 0.482763 1.135171 0.143 Uiso 0.433(8) 1 calc GR . P A 2
H22C H 0.619336 0.591045 1.101160 0.143 Uiso 0.433(8) 1 calc GR . P A 2
C21A C 0.8270(18) 0.612(2) 1.0317(14) 0.120(4) Uani 0.567(8) 1 d . U P A 1
H21D H 0.912140 0.585936 1.000986 0.179 Uiso 0.567(8) 1 calc GR . P A 1
H21E H 0.832268 0.594937 1.111279 0.179 Uiso 0.567(8) 1 calc GR . P A 1
H21F H 0.808306 0.712478 1.017206 0.179 Uiso 0.567(8) 1 calc GR . P A 1
C22A C 0.6213(19) 0.5253(18) 1.0760(9) 0.107(4) Uani 0.567(8) 1 d . U P A 1
H22D H 0.595869 0.623397 1.092001 0.160 Uiso 0.567(8) 1 calc GR . P A 1
H22E H 0.665806 0.482862 1.141749 0.160 Uiso 0.567(8) 1 calc GR . P A 1
H22F H 0.541151 0.470178 1.054474 0.160 Uiso 0.567(8) 1 calc GR . P A 1
C23 C 0.7254(5) 0.3772(6) 0.9302(4) 0.0663(11) Uani 1 1 d . U . . .
C24 C 0.8700(11) 0.3790(17) 0.8879(10) 0.094(3) Uani 0.567(8) 1 d . U P A 1
H24A H 0.875535 0.311696 0.826810 0.141 Uiso 0.567(8) 1 calc GR . P A 1
H24B H 0.934001 0.351740 0.947843 0.141 Uiso 0.567(8) 1 calc GR . P A 1
H24C H 0.891046 0.474856 0.862358 0.141 Uiso 0.567(8) 1 calc GR . P A 1
C25 C 0.7240(13) 0.2445(13) 0.9886(10) 0.092(3) Uani 0.567(8) 1 d . U P A 1
H25A H 0.699712 0.167629 0.936936 0.137 Uiso 0.567(8) 1 calc GR . P A 1
H25B H 0.658472 0.249236 1.045476 0.137 Uiso 0.567(8) 1 calc GR . P A 1
H25C H 0.812901 0.226038 1.023100 0.137 Uiso 0.567(8) 1 calc GR . P A 1
C24A C 0.8391(17) 0.2820(18) 0.9350(13) 0.095(3) Uani 0.433(8) 1 d . U P A 2
H24D H 0.808941 0.185183 0.917261 0.142 Uiso 0.433(8) 1 calc GR . P A 2
H24E H 0.882021 0.283630 1.009309 0.142 Uiso 0.433(8) 1 calc GR . P A 2
H24F H 0.903254 0.312639 0.881771 0.142 Uiso 0.433(8) 1 calc GR . P A 2
C25A C 0.6034(19) 0.283(2) 0.9750(15) 0.105(3) Uani 0.433(8) 1 d . U P A 2
H25D H 0.547255 0.343834 1.019203 0.157 Uiso 0.433(8) 1 calc GR . P A 2
H25E H 0.639814 0.205185 1.020482 0.157 Uiso 0.433(8) 1 calc GR . P A 2
H25F H 0.549605 0.244851 0.912328 0.157 Uiso 0.433(8) 1 calc GR . P A 2


_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
F1 C19 1.370(5) . ?
O1 C2 1.239(4) . ?
N2 H2 0.8800 . ?
N2 C1 1.461(4) . ?
N2 C2 1.329(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C7 1.514(5) . ?
C2 C3 1.523(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.528(4) . ?
C3 C13 1.547(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C7 C8 1.387(5) . ?
C7 C12 1.379(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.404(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.351(8) . ?
C10 H10 0.9500 . ?
C10 C11 1.375(8) . ?
C11 H11 0.9500 . ?
C11 C12 1.372(6) . ?
C12 H12 0.9500 . ?
C13 H13 1.0000 . ?
C13 C14 1.516(5) . ?
C13 B1 1.581(5) . ?
C14 C15 1.387(6) . ?
C14 C19 1.384(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.392(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.389(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.365(8) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(6) . ?
C20 O2 1.466(6) . ?
C20 C21 1.619(17) . ?
C20 C22 1.368(15) . ?
C20 C21A 1.475(16) . ?
C20 C22A 1.565(13) . ?
C20 C23 1.513(8) . ?
B1 O2 1.331(5) . ?
B1 O3 1.340(5) . ?
O3 C23 1.423(5) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C21A H21D 0.9800 . ?
C21A H21E 0.9800 . ?
C21A H21F 0.9800 . ?
C22A H22D 0.9800 . ?
C22A H22E 0.9800 . ?
C22A H22F 0.9800 . ?
C23 C24 1.564(12) . ?
C23 C25 1.437(12) . ?
C23 C24A 1.449(15) . ?
C23 C25A 1.624(18) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C24A H24D 0.9800 . ?
C24A H24E 0.9800 . ?
C24A H24F 0.9800 . ?
C25A H25D 0.9800 . ?
C25A H25E 0.9800 . ?
C25A H25F 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 N2 H2 118.8 . . ?
C2 N2 H2 118.8 . . ?
C2 N2 C1 122.4(3) . . ?
N2 C1 H1A 108.8 . . ?
N2 C1 H1B 108.8 . . ?
N2 C1 C7 113.7(2) . . ?
H1A C1 H1B 107.7 . . ?
C7 C1 H1A 108.8 . . ?
C7 C1 H1B 108.8 . . ?
O1 C2 N2 122.5(3) . . ?
O1 C2 C3 121.2(3) . . ?
N2 C2 C3 116.2(3) . . ?
C2 C3 H3 109.1 . . ?
C2 C3 C4 108.1(3) . . ?
C2 C3 C13 109.8(2) . . ?
C4 C3 H3 109.1 . . ?
C4 C3 C13 111.6(3) . . ?
C13 C3 H3 109.1 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C8 C7 C1 120.5(3) . . ?
C12 C7 C1 121.1(3) . . ?
C12 C7 C8 118.4(4) . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C9 119.0(4) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 119.1 . . ?
C10 C9 C8 121.9(4) . . ?
C10 C9 H9 119.1 . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.6(4) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.7(5) . . ?
C12 C11 H11 119.6 . . ?
C7 C12 H12 119.4 . . ?
C11 C12 C7 121.3(4) . . ?
C11 C12 H12 119.4 . . ?
C3 C13 H13 108.2 . . ?
C3 C13 B1 111.2(3) . . ?
C14 C13 C3 110.6(2) . . ?
C14 C13 H13 108.2 . . ?
C14 C13 B1 110.3(3) . . ?
B1 C13 H13 108.2 . . ?
C15 C14 C13 121.5(3) . . ?
C19 C14 C13 122.8(3) . . ?
C19 C14 C15 115.6(3) . . ?
C14 C15 H15 118.8 . . ?
C14 C15 C16 122.3(4) . . ?
C16 C15 H15 118.8 . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.4(4) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.9(4) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 120.4 . . ?
C17 C18 C19 119.1(4) . . ?
C19 C18 H18 120.4 . . ?
F1 C19 C14 118.3(3) . . ?
F1 C19 C18 118.0(4) . . ?
C18 C19 C14 123.7(4) . . ?
O2 C20 C21 101.4(7) . . ?
O2 C20 C21A 111.8(8) . . ?
O2 C20 C22A 99.4(7) . . ?
O2 C20 C23 103.6(3) . . ?
C22 C20 O2 117.4(9) . . ?
C22 C20 C21 99.9(13) . . ?
C22 C20 C23 129.2(10) . . ?
C21A C20 C22A 98.6(11) . . ?
C21A C20 C23 129.4(10) . . ?
C23 C20 C21 100.0(10) . . ?
C23 C20 C22A 110.1(8) . . ?
O2 B1 C13 123.0(3) . . ?
O2 B1 O3 112.8(3) . . ?
O3 B1 C13 124.1(3) . . ?
B1 O2 C20 108.7(3) . . ?
B1 O3 C23 109.9(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C21A H21D 109.5 . . ?
C20 C21A H21E 109.5 . . ?
C20 C21A H21F 109.5 . . ?
H21D C21A H21E 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
C20 C22A H22D 109.5 . . ?
C20 C22A H22E 109.5 . . ?
C20 C22A H22F 109.5 . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
C20 C23 C24 100.4(8) . . ?
C20 C23 C25A 108.3(9) . . ?
O3 C23 C20 104.9(3) . . ?
O3 C23 C24 98.1(5) . . ?
O3 C23 C25 118.9(6) . . ?
O3 C23 C24A 116.1(7) . . ?
O3 C23 C25A 89.0(7) . . ?
C25 C23 C20 126.7(6) . . ?
C25 C23 C24 101.9(8) . . ?
C24A C23 C20 126.9(8) . . ?
C24A C23 C25A 104.8(12) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C24A H24D 109.5 . . ?
C23 C24A H24E 109.5 . . ?
C23 C24A H24F 109.5 . . ?
H24D C24A H24E 109.5 . . ?
H24D C24A H24F 109.5 . . ?
H24E C24A H24F 109.5 . . ?
C23 C25A H25D 109.5 . . ?
C23 C25A H25E 109.5 . . ?
C23 C25A H25F 109.5 . . ?
H25D C25A H25E 109.5 . . ?
H25D C25A H25F 109.5 . . ?
H25E C25A H25F 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
O1 C2 C3 C4 -69.6(4) . . . . ?
O1 C2 C3 C13 52.4(4) . . . . ?
N2 C1 C7 C8 -128.2(3) . . . . ?
N2 C1 C7 C12 53.8(5) . . . . ?
N2 C2 C3 C4 108.6(3) . . . . ?
N2 C2 C3 C13 -129.4(3) . . . . ?
C1 N2 C2 O1 2.7(4) . . . . ?
C1 N2 C2 C3 -175.5(3) . . . . ?
C1 C7 C8 C9 -179.1(3) . . . . ?
C1 C7 C12 C11 178.9(5) . . . . ?
C2 N2 C1 C7 -94.3(3) . . . . ?
C2 C3 C13 C14 56.1(3) . . . . ?
C2 C3 C13 B1 179.0(3) . . . . ?
C3 C13 C14 C15 59.1(4) . . . . ?
C3 C13 C14 C19 -118.2(3) . . . . ?
C3 C13 B1 O2 134.2(4) . . . . ?
C3 C13 B1 O3 -45.2(5) . . . . ?
C4 C3 C13 C14 176.0(3) . . . . ?
C4 C3 C13 B1 -61.1(4) . . . . ?
C7 C8 C9 C10 -0.1(7) . . . . ?
C8 C7 C12 C11 0.9(7) . . . . ?
C8 C9 C10 C11 1.5(8) . . . . ?
C9 C10 C11 C12 -1.7(9) . . . . ?
C10 C11 C12 C7 0.5(9) . . . . ?
C12 C7 C8 C9 -1.1(6) . . . . ?
C13 C14 C15 C16 -175.9(3) . . . . ?
C13 C14 C19 F1 -3.2(5) . . . . ?
C13 C14 C19 C18 176.8(3) . . . . ?
C13 B1 O2 C20 -176.6(4) . . . . ?
C13 B1 O3 C23 177.7(4) . . . . ?
C14 C13 B1 O2 -102.8(4) . . . . ?
C14 C13 B1 O3 77.8(5) . . . . ?
C14 C15 C16 C17 -0.9(6) . . . . ?
C15 C14 C19 F1 179.3(3) . . . . ?
C15 C14 C19 C18 -0.7(5) . . . . ?
C15 C16 C17 C18 -0.9(7) . . . . ?
C16 C17 C18 C19 1.8(7) . . . . ?
C17 C18 C19 F1 179.0(4) . . . . ?
C17 C18 C19 C14 -1.0(7) . . . . ?
C19 C14 C15 C16 1.6(5) . . . . ?
B1 C13 C14 C15 -64.3(4) . . . . ?
B1 C13 C14 C19 118.4(3) . . . . ?
B1 O3 C23 C20 -0.1(6) . . . . ?
B1 O3 C23 C24 -103.2(7) . . . . ?
B1 O3 C23 C25 148.3(8) . . . . ?
B1 O3 C23 C24A -145.4(10) . . . . ?
B1 O3 C23 C25A 108.6(9) . . . . ?
O2 C20 C23 O3 1.7(6) . . . . ?
O2 C20 C23 C24 103.1(6) . . . . ?
O2 C20 C23 C25 -143.5(8) . . . . ?
O2 C20 C23 C24A 142.0(10) . . . . ?
O2 C20 C23 C25A -92.3(7) . . . . ?
O2 B1 O3 C23 -1.7(6) . . . . ?
O3 B1 O2 C20 2.9(6) . . . . ?
C21 C20 O2 B1 100.7(10) . . . . ?
C21 C20 C23 O3 -102.8(7) . . . . ?
C21 C20 C23 C24A 37.5(12) . . . . ?
C21 C20 C23 C25A 163.3(8) . . . . ?
C22 C20 O2 B1 -151.8(13) . . . . ?
C22 C20 C23 O3 145.6(13) . . . . ?
C22 C20 C23 C24A -74.2(17) . . . . ?
C22 C20 C23 C25A 51.6(15) . . . . ?
C21A C20 O2 B1 140.4(10) . . . . ?
C21A C20 C23 O3 -132.3(10) . . . . ?
C21A C20 C23 C24 -30.9(11) . . . . ?
C21A C20 C23 C25 82.6(13) . . . . ?
C22A C20 O2 B1 -116.3(8) . . . . ?
C22A C20 C23 O3 107.2(8) . . . . ?
C22A C20 C23 C24 -151.4(8) . . . . ?
C22A C20 C23 C25 -38.0(11) . . . . ?
C23 C20 O2 B1 -2.7(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
