# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_210907_s2_wtb
_database_code_depnum_ccdc_archive 'CCDC 2114141'
loop_
_audit_author_name
_audit_author_address
'wang tianbao'
;sichuan university
China
;
_audit_update_record             
;
2021-10-06 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;
_audit_creation_date             2021-09-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C F3 O3 S, C33 H19 N2'
_chemical_formula_sum            'C34 H19 F3 N2 O3 S'
_chemical_formula_weight         592.57
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3s1
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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3567(6)
_cell_length_b                   10.7079(6)
_cell_length_c                   14.3234(8)
_cell_angle_alpha                81.633(5)
_cell_angle_beta                 87.519(5)
_cell_angle_gamma                83.289(5)
_cell_volume                     1409.56(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2594
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3180
_cell_measurement_theta_min      3.2420
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11362
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.952
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -83.00    1.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  -57.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega  -23.00    5.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  -99.0000    0.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega  -21.00   21.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  -99.0000 -180.0000 42

#__ type_ start__ end____ width___ exp.time_
  4 omega  -21.00   35.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6648  -99.0000 -180.0000 56

#__ type_ start__ end____ width___ exp.time_
  5 omega   -1.00   87.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6648   38.0000    0.0000 88

#__ type_ start__ end____ width___ exp.time_
  6 omega  -54.00   37.00   1.0000    8.5000
omega____ theta____ kappa____ phi______ frames
    -       17.6648  -19.0000 -180.0000 91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0755172000
_diffrn_orient_matrix_UB_12      0.0016017000
_diffrn_orient_matrix_UB_13      -0.0039471000
_diffrn_orient_matrix_UB_21      0.0053110000
_diffrn_orient_matrix_UB_22      -0.0665929000
_diffrn_orient_matrix_UB_23      0.0143416000
_diffrn_orient_matrix_UB_31      -0.0099667000
_diffrn_orient_matrix_UB_32      0.0101198000
_diffrn_orient_matrix_UB_33      0.0478104000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3522
_reflns_number_total             5757
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.992
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5757
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1117
_refine_ls_R_factor_gt           0.0749
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1137P)²+0.2339P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2067
_refine_ls_wR_factor_ref         0.2298
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16), C22(H22), C23(H23), C24(H24), C25(H25), C28(H28), C29(H29),
  C30(H30), C31(H31)
;
_atom_sites_solution_hydrogens   geom
_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
S2 S 0.75943(11) 0.27670(11) 0.24771(6) 0.0690(4) Uani 1 1 d . . . . .
F1 F 0.8916(4) 0.3326(4) 0.3885(2) 0.1451(15) Uani 1 1 d . . . . .
F2 F 0.8018(6) 0.4902(4) 0.2965(3) 0.180(2) Uani 1 1 d . . . . .
F3 F 0.9898(4) 0.3845(5) 0.2527(3) 0.1747(19) Uani 1 1 d . . . . .
O1 O 0.6377(3) 0.2670(3) 0.31093(18) 0.0790(9) Uani 1 1 d . . . . .
O2 O 0.8546(5) 0.1595(4) 0.2480(3) 0.1233(14) Uani 1 1 d . . . . .
O3 O 0.7336(4) 0.3338(4) 0.1547(2) 0.1143(14) Uani 1 1 d . . . . .
C34 C 0.8682(6) 0.3740(5) 0.2996(4) 0.0904(15) Uani 1 1 d . . . . .
N1 N 0.5017(3) 0.1097(2) 0.15532(16) 0.0377(6) Uani 1 1 d . . . . .
N2 N 0.6883(3) -0.0356(2) 0.14796(16) 0.0399(6) Uani 1 1 d . . . . .
C1 C 0.4263(3) 0.2337(3) 0.1246(2) 0.0427(7) Uani 1 1 d . . . . .
C2 C 0.3530(4) 0.3042(3) 0.1886(2) 0.0499(8) Uani 1 1 d . . . . .
H2 H 0.349406 0.271898 0.252395 0.060 Uiso 1 1 calc R . . . .
C3 C 0.2851(4) 0.4231(3) 0.1567(3) 0.0607(10) Uani 1 1 d . . . . .
H3 H 0.234883 0.471388 0.198958 0.073 Uiso 1 1 calc R . . . .
C4 C 0.2919(4) 0.4700(4) 0.0622(3) 0.0638(10) Uani 1 1 d . . . . .
H4 H 0.240985 0.548073 0.040885 0.077 Uiso 1 1 calc R . . . .
C5 C 0.3712(4) 0.4052(4) -0.0012(3) 0.0576(9) Uani 1 1 d . . . . .
H5 H 0.376983 0.440804 -0.064226 0.069 Uiso 1 1 calc R . . . .
C6 C 0.4441(4) 0.2846(3) 0.0288(2) 0.0485(8) Uani 1 1 d . . . . .
C7 C 0.5485(4) 0.2225(3) -0.0338(2) 0.0488(8) Uani 1 1 d . . . . .
C8 C 0.5762(5) 0.2685(4) -0.1288(2) 0.0677(11) Uani 1 1 d . . . . .
H8 H 0.517515 0.336883 -0.159528 0.081 Uiso 1 1 calc R . . . .
C9 C 0.6923(5) 0.2110(4) -0.1763(3) 0.0723(13) Uani 1 1 d . . . . .
H9 H 0.711117 0.243631 -0.238876 0.087 Uiso 1 1 calc R . . . .
C10 C 0.7802(5) 0.1086(4) -0.1356(2) 0.0623(11) Uani 1 1 d . . . . .
H10 H 0.858780 0.075263 -0.169682 0.075 Uiso 1 1 calc R . . . .
C11 C 0.7529(4) 0.0538(3) -0.0431(2) 0.0499(9) Uani 1 1 d . . . . .
C12 C 0.8260(3) -0.0646(3) 0.0041(2) 0.0487(8) Uani 1 1 d . . . . .
C13 C 0.9261(4) -0.1431(4) -0.0451(3) 0.0618(10) Uani 1 1 d . . . . .
H13 H 0.957144 -0.112443 -0.105783 0.074 Uiso 1 1 calc R . . . .
C14 C 0.9784(4) -0.2635(5) -0.0052(3) 0.0715(12) Uani 1 1 d . . . . .
H14 H 1.046070 -0.312415 -0.038068 0.086 Uiso 1 1 calc R . . . .
C15 C 0.9301(4) -0.3117(4) 0.0838(3) 0.0629(10) Uani 1 1 d . . . . .
H15 H 0.962078 -0.394622 0.109352 0.075 Uiso 1 1 calc R . . . .
C16 C 0.8356(4) -0.2386(3) 0.1350(3) 0.0526(8) Uani 1 1 d . . . . .
H16 H 0.803046 -0.272169 0.194614 0.063 Uiso 1 1 calc R . . . .
C17 C 0.7888(3) -0.1147(3) 0.0976(2) 0.0447(8) Uani 1 1 d . . . . .
C18 C 0.6098(3) 0.0658(3) 0.09981(19) 0.0390(7) Uani 1 1 d . . . . .
C19 C 0.6371(3) 0.1139(3) 0.0061(2) 0.0431(8) Uani 1 1 d . . . . .
C20 C 0.5064(3) 0.0303(3) 0.24169(19) 0.0375(7) Uani 1 1 d . . . . .
C21 C 0.3968(3) 0.0112(3) 0.31528(19) 0.0383(7) Uani 1 1 d . . . . .
C22 C 0.2520(3) 0.0591(3) 0.3058(2) 0.0461(8) Uani 1 1 d . . . . .
H22 H 0.224336 0.115859 0.252473 0.055 Uiso 1 1 calc R . . . .
C23 C 0.1494(4) 0.0247(3) 0.3732(2) 0.0563(9) Uani 1 1 d . . . . .
H23 H 0.052963 0.055368 0.364737 0.068 Uiso 1 1 calc R . . . .
C24 C 0.1921(4) -0.0569(4) 0.4543(3) 0.0624(10) Uani 1 1 d . . . . .
H24 H 0.124278 -0.077397 0.501752 0.075 Uiso 1 1 calc R . . . .
C25 C 0.3323(4) -0.1073(3) 0.4650(2) 0.0565(9) Uani 1 1 d . . . . .
H25 H 0.357568 -0.163059 0.519248 0.068 Uiso 1 1 calc R . . . .
C26 C 0.4394(4) -0.0774(3) 0.3965(2) 0.0424(7) Uani 1 1 d . . . . .
C27 C 0.5873(4) -0.1376(3) 0.4047(2) 0.0429(7) Uani 1 1 d . . . . .
C28 C 0.6395(4) -0.2045(3) 0.4905(2) 0.0542(9) Uani 1 1 d . . . . .
H28 H 0.576691 -0.214737 0.542435 0.065 Uiso 1 1 calc R . . . .
C29 C 0.7789(5) -0.2545(4) 0.4995(3) 0.0650(10) Uani 1 1 d . . . . .
H29 H 0.809550 -0.299638 0.556955 0.078 Uiso 1 1 calc R . . . .
C30 C 0.8768(4) -0.2390(4) 0.4239(3) 0.0604(9) Uani 1 1 d . . . . .
H30 H 0.972537 -0.272706 0.431262 0.072 Uiso 1 1 calc R . . . .
C31 C 0.8317(4) -0.1733(3) 0.3378(2) 0.0544(9) Uani 1 1 d . . . . .
H31 H 0.897558 -0.160477 0.287753 0.065 Uiso 1 1 calc R . . . .
C32 C 0.6848(3) -0.1258(3) 0.3261(2) 0.0431(7) Uani 1 1 d . . . . .
C33 C 0.6290(3) -0.0521(3) 0.24116(19) 0.0388(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 O1 1.428(3) . ?
S2 O2 1.451(4) . ?
S2 O3 1.401(3) . ?
S2 C34 1.793(5) . ?
F1 C34 1.305(6) . ?
F2 C34 1.320(6) . ?
F3 C34 1.304(5) . ?
N1 C1 1.447(4) . ?
N1 C18 1.343(4) . ?
N1 C20 1.395(4) . ?
N2 C17 1.433(4) . ?
N2 C18 1.354(4) . ?
N2 C33 1.418(3) . ?
C1 C2 1.381(5) . ?
C1 C6 1.411(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.364(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.405(5) . ?
C6 C7 1.465(5) . ?
C7 C8 1.402(5) . ?
C7 C19 1.409(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.388(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.365(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.395(5) . ?
C11 C12 1.456(5) . ?
C11 C19 1.410(5) . ?
C12 C13 1.419(5) . ?
C12 C17 1.413(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.371(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.384(5) . ?
C18 C19 1.391(4) . ?
C20 C21 1.448(4) . ?
C20 C33 1.364(4) . ?
C21 C22 1.397(4) . ?
C21 C26 1.429(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.375(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.391(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.365(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.403(4) . ?
C26 C27 1.459(5) . ?
C27 C28 1.406(5) . ?
C27 C32 1.418(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.355(5) . ?
C29 H29 0.9300 . ?
C29 C30 1.392(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.385(5) . ?
C31 H31 0.9300 . ?
C31 C32 1.417(5) . ?
C32 C33 1.434(4) . ?

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
O1 S2 O2 114.4(2) . . ?
O1 S2 C34 103.9(2) . . ?
O2 S2 C34 102.1(3) . . ?
O3 S2 O1 117.3(2) . . ?
O3 S2 O2 110.0(3) . . ?
O3 S2 C34 107.5(3) . . ?
F1 C34 S2 112.3(3) . . ?
F1 C34 F2 106.3(5) . . ?
F2 C34 S2 110.0(4) . . ?
F3 C34 S2 111.2(4) . . ?
F3 C34 F1 110.4(5) . . ?
F3 C34 F2 106.4(4) . . ?
C18 N1 C1 118.0(2) . . ?
C18 N1 C20 107.9(2) . . ?
C20 N1 C1 132.9(2) . . ?
C18 N2 C17 119.5(2) . . ?
C18 N2 C33 106.9(2) . . ?
C33 N2 C17 132.5(3) . . ?
C2 C1 N1 121.0(3) . . ?
C2 C1 C6 121.6(3) . . ?
C6 C1 N1 117.1(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.8(4) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.9(4) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C7 121.4(3) . . ?
C5 C6 C1 117.2(3) . . ?
C5 C6 C7 120.9(3) . . ?
C8 C7 C6 125.1(4) . . ?
C8 C7 C19 116.9(3) . . ?
C19 C7 C6 117.8(3) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.3(4) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 H9 118.5 . . ?
C10 C9 C8 123.0(3) . . ?
C10 C9 H9 118.5 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.4(4) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 125.8(3) . . ?
C10 C11 C19 116.6(4) . . ?
C19 C11 C12 117.5(3) . . ?
C13 C12 C11 121.4(3) . . ?
C17 C12 C11 121.9(3) . . ?
C17 C12 C13 116.3(3) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 C12 121.5(3) . . ?
C14 C13 H13 119.2 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.8(3) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.8(4) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C12 C17 N2 116.6(3) . . ?
C16 C17 N2 121.7(3) . . ?
C16 C17 C12 121.4(3) . . ?
N1 C18 N2 109.9(2) . . ?
N1 C18 C19 125.9(3) . . ?
N2 C18 C19 124.2(3) . . ?
C7 C19 C11 123.7(3) . . ?
C18 C19 C7 117.7(3) . . ?
C18 C19 C11 118.6(3) . . ?
N1 C20 C21 130.6(3) . . ?
C33 C20 N1 107.7(2) . . ?
C33 C20 C21 120.7(3) . . ?
C22 C21 C20 124.3(3) . . ?
C22 C21 C26 119.3(3) . . ?
C26 C21 C20 115.8(3) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 C21 121.7(3) . . ?
C23 C22 H22 119.1 . . ?
C22 C23 H23 120.6 . . ?
C22 C23 C24 118.9(4) . . ?
C24 C23 H23 120.6 . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.8(3) . . ?
C25 C24 H24 119.6 . . ?
C24 C25 H25 119.0 . . ?
C24 C25 C26 121.9(3) . . ?
C26 C25 H25 119.0 . . ?
C21 C26 C27 120.7(3) . . ?
C25 C26 C21 117.3(3) . . ?
C25 C26 C27 122.0(3) . . ?
C28 C27 C26 121.7(3) . . ?
C28 C27 C32 117.9(3) . . ?
C32 C27 C26 120.3(3) . . ?
C27 C28 H28 119.1 . . ?
C29 C28 C27 121.8(3) . . ?
C29 C28 H28 119.1 . . ?
C28 C29 H29 119.6 . . ?
C28 C29 C30 120.8(4) . . ?
C30 C29 H29 119.6 . . ?
C29 C30 H30 120.0 . . ?
C31 C30 C29 120.0(4) . . ?
C31 C30 H30 120.0 . . ?
C30 C31 H31 120.1 . . ?
C30 C31 C32 119.7(3) . . ?
C32 C31 H31 120.1 . . ?
C27 C32 C33 116.1(3) . . ?
C31 C32 C27 119.6(3) . . ?
C31 C32 C33 123.8(3) . . ?
N2 C33 C32 130.9(3) . . ?
C20 C33 N2 106.9(3) . . ?
C20 C33 C32 121.8(3) . . ?

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 S2 C34 F1 51.4(5) . . . . ?
O1 S2 C34 F2 -66.8(4) . . . . ?
O1 S2 C34 F3 175.6(4) . . . . ?
O2 S2 C34 F1 -67.8(5) . . . . ?
O2 S2 C34 F2 174.0(4) . . . . ?
O2 S2 C34 F3 56.4(5) . . . . ?
O3 S2 C34 F1 176.3(4) . . . . ?
O3 S2 C34 F2 58.2(4) . . . . ?
O3 S2 C34 F3 -59.4(5) . . . . ?
N1 C1 C2 C3 178.6(3) . . . . ?
N1 C1 C6 C5 -179.9(3) . . . . ?
N1 C1 C6 C7 -7.7(4) . . . . ?
N1 C18 C19 C7 3.4(4) . . . . ?
N1 C18 C19 C11 -178.0(3) . . . . ?
N1 C20 C21 C22 10.1(5) . . . . ?
N1 C20 C21 C26 -179.0(3) . . . . ?
N1 C20 C33 N2 -8.9(3) . . . . ?
N1 C20 C33 C32 164.7(2) . . . . ?
N2 C18 C19 C7 -178.1(3) . . . . ?
N2 C18 C19 C11 0.5(4) . . . . ?
C1 N1 C18 N2 166.1(2) . . . . ?
C1 N1 C18 C19 -15.2(4) . . . . ?
C1 N1 C20 C21 33.1(5) . . . . ?
C1 N1 C20 C33 -159.1(3) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C1 C6 C7 C8 -177.9(3) . . . . ?
C1 C6 C7 C19 -3.6(4) . . . . ?
C2 C1 C6 C5 -6.6(4) . . . . ?
C2 C1 C6 C7 165.5(3) . . . . ?
C2 C3 C4 C5 -3.8(5) . . . . ?
C3 C4 C5 C6 2.7(5) . . . . ?
C4 C5 C6 C1 2.4(5) . . . . ?
C4 C5 C6 C7 -169.7(3) . . . . ?
C5 C6 C7 C8 -6.0(5) . . . . ?
C5 C6 C7 C19 168.2(3) . . . . ?
C6 C1 C2 C3 5.6(5) . . . . ?
C6 C7 C8 C9 170.5(3) . . . . ?
C6 C7 C19 C11 -172.3(3) . . . . ?
C6 C7 C19 C18 6.2(4) . . . . ?
C7 C8 C9 C10 1.6(6) . . . . ?
C8 C7 C19 C11 2.4(4) . . . . ?
C8 C7 C19 C18 -179.1(3) . . . . ?
C8 C9 C10 C11 2.3(6) . . . . ?
C9 C10 C11 C12 171.4(3) . . . . ?
C9 C10 C11 C19 -3.6(5) . . . . ?
C10 C11 C12 C13 -6.1(5) . . . . ?
C10 C11 C12 C17 -178.5(3) . . . . ?
C10 C11 C19 C7 1.2(4) . . . . ?
C10 C11 C19 C18 -177.3(3) . . . . ?
C11 C12 C13 C14 -169.8(3) . . . . ?
C11 C12 C17 N2 -7.6(4) . . . . ?
C11 C12 C17 C16 166.0(3) . . . . ?
C12 C11 C19 C7 -174.2(3) . . . . ?
C12 C11 C19 C18 7.4(4) . . . . ?
C12 C13 C14 C15 1.9(5) . . . . ?
C13 C12 C17 N2 179.7(3) . . . . ?
C13 C12 C17 C16 -6.8(4) . . . . ?
C13 C14 C15 C16 -3.1(6) . . . . ?
C14 C15 C16 C17 -0.6(5) . . . . ?
C15 C16 C17 N2 179.0(3) . . . . ?
C15 C16 C17 C12 5.8(5) . . . . ?
C17 N2 C18 N1 166.4(2) . . . . ?
C17 N2 C18 C19 -12.3(4) . . . . ?
C17 N2 C33 C20 -159.9(3) . . . . ?
C17 N2 C33 C32 27.2(5) . . . . ?
C17 C12 C13 C14 3.0(5) . . . . ?
C18 N1 C1 C2 -156.7(3) . . . . ?
C18 N1 C1 C6 16.7(4) . . . . ?
C18 N1 C20 C21 -160.4(3) . . . . ?
C18 N1 C20 C33 7.3(3) . . . . ?
C18 N2 C17 C12 15.3(4) . . . . ?
C18 N2 C17 C16 -158.2(3) . . . . ?
C18 N2 C33 C20 7.4(3) . . . . ?
C18 N2 C33 C32 -165.5(3) . . . . ?
C19 C7 C8 C9 -3.8(5) . . . . ?
C19 C11 C12 C13 168.8(3) . . . . ?
C19 C11 C12 C17 -3.6(4) . . . . ?
C20 N1 C1 C2 8.7(5) . . . . ?
C20 N1 C1 C6 -178.0(3) . . . . ?
C20 N1 C18 N2 -2.6(3) . . . . ?
C20 N1 C18 C19 176.0(3) . . . . ?
C20 C21 C22 C23 171.5(3) . . . . ?
C20 C21 C26 C25 -174.0(3) . . . . ?
C20 C21 C26 C27 3.3(4) . . . . ?
C21 C20 C33 N2 160.3(2) . . . . ?
C21 C20 C33 C32 -26.1(4) . . . . ?
C21 C22 C23 C24 2.1(5) . . . . ?
C21 C26 C27 C28 167.0(3) . . . . ?
C21 C26 C27 C32 -10.5(4) . . . . ?
C22 C21 C26 C25 -2.7(4) . . . . ?
C22 C21 C26 C27 174.6(3) . . . . ?
C22 C23 C24 C25 -3.3(5) . . . . ?
C23 C24 C25 C26 1.4(6) . . . . ?
C24 C25 C26 C21 1.6(5) . . . . ?
C24 C25 C26 C27 -175.7(3) . . . . ?
C25 C26 C27 C28 -15.8(5) . . . . ?
C25 C26 C27 C32 166.7(3) . . . . ?
C26 C21 C22 C23 0.9(4) . . . . ?
C26 C27 C28 C29 -176.3(3) . . . . ?
C26 C27 C32 C31 173.4(3) . . . . ?
C26 C27 C32 C33 0.3(4) . . . . ?
C27 C28 C29 C30 1.3(6) . . . . ?
C27 C32 C33 N2 -170.1(3) . . . . ?
C27 C32 C33 C20 17.9(4) . . . . ?
C28 C27 C32 C31 -4.2(4) . . . . ?
C28 C27 C32 C33 -177.3(3) . . . . ?
C28 C29 C30 C31 -0.9(6) . . . . ?
C29 C30 C31 C32 -2.1(5) . . . . ?
C30 C31 C32 C27 4.7(5) . . . . ?
C30 C31 C32 C33 177.2(3) . . . . ?
C31 C32 C33 N2 17.1(5) . . . . ?
C31 C32 C33 C20 -154.8(3) . . . . ?
C32 C27 C28 C29 1.3(5) . . . . ?
C33 N2 C17 C12 -178.7(3) . . . . ?
C33 N2 C17 C16 7.8(5) . . . . ?
C33 N2 C18 N1 -2.9(3) . . . . ?
C33 N2 C18 C19 178.4(3) . . . . ?
C33 C20 C21 C22 -156.3(3) . . . . ?
C33 C20 C21 C26 14.5(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_mo_wtb_3_2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2114143'
loop_
_audit_author_name
_audit_author_address
'wang tianbao'
;sichuan university
China
;
_audit_update_record             
;
2021-10-06 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;
_audit_creation_date             2021-05-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'B F4, C25 H15 N2'
_chemical_formula_sum            'C25 H15 B F4 N2'
_chemical_formula_weight         430.20
_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'

_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.4814(4)
_cell_length_b                   14.5840(9)
_cell_length_c                   16.2845(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.547(2)
_cell_angle_gamma                90
_cell_volume                     1958.23(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9955
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      23.898
_cell_measurement_theta_min      2.573
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1095 before and 0.0637 after correction.
The Ratio of minimum to maximum transmission is 0.9409.
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    1.459
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.29
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0999
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            90776
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.537
_diffrn_reflns_theta_min         2.504
_diffrn_ambient_temperature      301.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2523
_reflns_number_total             4495
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.717
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4495
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1228
_refine_ls_R_factor_gt           0.0718
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1353P)²+0.6315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2064
_refine_ls_wR_factor_ref         0.2533
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23)
;
_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 0.6198(3) 0.34267(18) 0.2228(2) 0.1322(10) Uani 1 1 d . . . . .
F2 F 0.3910(3) 0.41008(17) 0.15766(15) 0.1165(8) Uani 1 1 d . . . . .
F3 F 0.5135(3) 0.45427(15) 0.28765(13) 0.0979(7) Uani 1 1 d . . . . .
F4 F 0.3851(3) 0.31678(18) 0.2612(2) 0.1256(9) Uani 1 1 d . . . . .
N1 N 0.8373(2) 0.53453(15) 0.37222(13) 0.0559(6) Uani 1 1 d . . . . .
N2 N 0.9227(3) 0.39422(15) 0.35022(14) 0.0573(6) Uani 1 1 d . . . . .
C1 C 0.6971(4) 0.7559(3) 0.4410(3) 0.0893(11) Uani 1 1 d . . . . .
H1 H 0.6892 0.8171 0.4244 0.107 Uiso 1 1 calc R U . . .
C2 C 0.7565(4) 0.6929(2) 0.3945(2) 0.0785(9) Uani 1 1 d . . . . .
H2 H 0.7879 0.7112 0.3459 0.094 Uiso 1 1 calc R U . . .
C3 C 0.7707(3) 0.60154(19) 0.41872(19) 0.0624(7) Uani 1 1 d . . . . .
C4 C 0.8529(3) 0.44725(18) 0.39991(16) 0.0546(6) Uani 1 1 d . . . . .
C5 C 0.9434(3) 0.29954(19) 0.36601(19) 0.0632(7) Uani 1 1 d . . . . .
C6 C 0.8979(3) 0.2629(2) 0.43677(18) 0.0653(7) Uani 1 1 d . . . . .
C7 C 0.9204(4) 0.1679(2) 0.4514(2) 0.0843(10) Uani 1 1 d . . . . .
H7 H 0.8917 0.1422 0.4980 0.101 Uiso 1 1 calc R U . . .
C8 C 0.9827(5) 0.1127(2) 0.3995(3) 0.0923(11) Uani 1 1 d . . . . .
H8 H 0.9960 0.0503 0.4108 0.111 Uiso 1 1 calc R U . . .
C9 C 0.6492(4) 0.7297(3) 0.5119(3) 0.0959(12) Uani 1 1 d . . . . .
H9 H 0.6077 0.7731 0.5430 0.115 Uiso 1 1 calc R U . . .
C10 C 0.6617(4) 0.6403(3) 0.5372(2) 0.0805(9) Uani 1 1 d . . . . .
H10 H 0.6288 0.6235 0.5857 0.097 Uiso 1 1 calc R U . . .
C11 C 0.7235(3) 0.5734(2) 0.49146(18) 0.0656(8) Uani 1 1 d . . . . .
C12 C 0.7397(3) 0.4776(2) 0.51957(18) 0.0654(8) Uani 1 1 d . . . . .
C13 C 0.6972(4) 0.4439(3) 0.5912(2) 0.0760(9) Uani 1 1 d . . . . .
H13 H 0.6517 0.4828 0.6246 0.091 Uiso 1 1 calc R U . . .
C14 C 0.7221(4) 0.3534(3) 0.6127(2) 0.0865(10) Uani 1 1 d . . . . .
H14 H 0.6947 0.3324 0.6615 0.104 Uiso 1 1 calc R U . . .
C15 C 0.7863(4) 0.2921(3) 0.5649(2) 0.0795(9) Uani 1 1 d . . . . .
H15 H 0.8006 0.2310 0.5814 0.095 Uiso 1 1 calc R U . . .
C16 C 0.8294(3) 0.3214(2) 0.49221(18) 0.0630(7) Uani 1 1 d . . . . .
C17 C 1.0260(5) 0.1499(2) 0.3302(3) 0.0921(11) Uani 1 1 d . . . . .
H17 H 1.0690 0.1125 0.2946 0.111 Uiso 1 1 calc R U . . .
C18 C 1.0062(4) 0.2403(2) 0.3138(2) 0.0799(9) Uani 1 1 d . . . . .
H18 H 1.0350 0.2641 0.2664 0.096 Uiso 1 1 calc R U . . .
C19 C 0.8993(3) 0.53955(19) 0.29906(18) 0.0607(7) Uani 1 1 d . . . . .
C20 C 0.9149(4) 0.6107(2) 0.2453(2) 0.0800(9) Uani 1 1 d . . . . .
H20 H 0.8751 0.6687 0.2527 0.096 Uiso 1 1 calc R U . . .
C21 C 0.9885(5) 0.5941(3) 0.1824(3) 0.0971(12) Uani 1 1 d . . . . .
H21 H 0.9977 0.6412 0.1454 0.116 Uiso 1 1 calc R U . . .
C22 C 1.0505(5) 0.5093(3) 0.1716(3) 0.0957(11) Uani 1 1 d . . . . .
H22 H 1.1046 0.5009 0.1286 0.115 Uiso 1 1 calc R U . . .
C23 C 1.0350(4) 0.4376(2) 0.2218(2) 0.0789(9) Uani 1 1 d . . . . .
H23 H 1.0763 0.3803 0.2134 0.095 Uiso 1 1 calc R U . . .
C24 C 0.9559(3) 0.4519(2) 0.28612(18) 0.0606(7) Uani 1 1 d . . . . .
C25 C 0.8049(3) 0.4146(2) 0.47147(16) 0.0581(7) Uani 1 1 d . . . . .
B1 B 0.4827(4) 0.3803(2) 0.2353(2) 0.0652(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.344(4) . ?
F2 B1 1.390(4) . ?
F3 B1 1.362(4) . ?
F4 B1 1.373(4) . ?
N1 C3 1.431(3) . ?
N1 C4 1.346(3) . ?
N1 C19 1.412(4) . ?
N2 C4 1.352(3) . ?
N2 C5 1.408(4) . ?
N2 C24 1.419(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.361(5) . ?
C1 C9 1.365(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(4) . ?
C3 C11 1.398(4) . ?
C4 C25 1.405(4) . ?
C5 C6 1.404(4) . ?
C5 C18 1.401(4) . ?
C6 C7 1.411(4) . ?
C6 C16 1.458(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.360(5) . ?
C8 H8 0.9300 . ?
C8 C17 1.378(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.364(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.401(4) . ?
C11 C12 1.467(5) . ?
C12 C13 1.390(4) . ?
C12 C25 1.403(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.369(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(4) . ?
C16 C25 1.404(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.349(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.383(4) . ?
C19 C24 1.399(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.340(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.372(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.352(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.385(4) . ?

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 C3 119.2(2) . . ?
C4 N1 C19 107.7(2) . . ?
C19 N1 C3 133.0(2) . . ?
C4 N2 C5 120.3(2) . . ?
C4 N2 C24 106.9(2) . . ?
C5 N2 C24 132.7(2) . . ?
C2 C1 H1 119.9 . . ?
C2 C1 C9 120.3(4) . . ?
C9 C1 H1 119.9 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.6(4) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 N1 121.6(3) . . ?
C2 C3 C11 120.0(3) . . ?
C11 C3 N1 118.4(3) . . ?
N1 C4 N2 111.3(2) . . ?
N1 C4 C25 125.0(2) . . ?
N2 C4 C25 123.7(3) . . ?
C6 C5 N2 118.4(3) . . ?
C18 C5 N2 122.9(3) . . ?
C18 C5 C6 118.7(3) . . ?
C5 C6 C7 117.3(3) . . ?
C5 C6 C16 120.8(3) . . ?
C7 C6 C16 121.9(3) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 C6 122.3(4) . . ?
C8 C7 H7 118.9 . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C17 119.5(3) . . ?
C17 C8 H8 120.2 . . ?
C1 C9 H9 119.8 . . ?
C10 C9 C1 120.4(3) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.1(4) . . ?
C11 C10 H10 119.4 . . ?
C3 C11 C10 117.6(3) . . ?
C3 C11 C12 121.3(3) . . ?
C10 C11 C12 121.1(3) . . ?
C13 C12 C11 125.1(3) . . ?
C13 C12 C25 116.8(3) . . ?
C25 C12 C11 118.1(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 118.7 . . ?
C13 C14 C15 122.6(3) . . ?
C15 C14 H14 118.7 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.1(3) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C6 124.9(3) . . ?
C15 C16 C25 116.7(3) . . ?
C25 C16 C6 118.4(3) . . ?
C8 C17 H17 120.0 . . ?
C18 C17 C8 120.1(4) . . ?
C18 C17 H17 120.0 . . ?
C5 C18 H18 119.0 . . ?
C17 C18 C5 122.1(3) . . ?
C17 C18 H18 119.0 . . ?
C20 C19 N1 133.0(3) . . ?
C20 C19 C24 120.2(3) . . ?
C24 C19 N1 106.8(2) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 C19 118.6(3) . . ?
C21 C20 H20 120.7 . . ?
C20 C21 H21 119.3 . . ?
C20 C21 C22 121.5(3) . . ?
C22 C21 H21 119.3 . . ?
C21 C22 H22 119.2 . . ?
C23 C22 C21 121.6(3) . . ?
C23 C22 H22 119.2 . . ?
C22 C23 H23 120.8 . . ?
C22 C23 C24 118.3(3) . . ?
C24 C23 H23 120.8 . . ?
C19 C24 N2 107.2(2) . . ?
C23 C24 N2 133.0(3) . . ?
C23 C24 C19 119.7(3) . . ?
C12 C25 C4 118.0(3) . . ?
C12 C25 C16 123.8(3) . . ?
C16 C25 C4 118.2(3) . . ?
F1 B1 F2 108.0(3) . . ?
F1 B1 F3 111.9(3) . . ?
F1 B1 F4 112.1(3) . . ?
F3 B1 F2 107.9(3) . . ?
F3 B1 F4 112.6(3) . . ?
F4 B1 F2 103.9(3) . . ?

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 C3 C11 C10 178.7(2) . . . . ?
N1 C3 C11 C12 -0.6(4) . . . . ?
N1 C4 C25 C12 -1.9(4) . . . . ?
N1 C4 C25 C16 -180.0(2) . . . . ?
N1 C19 C20 C21 176.3(3) . . . . ?
N1 C19 C24 N2 1.8(3) . . . . ?
N1 C19 C24 C23 -175.2(2) . . . . ?
N2 C4 C25 C12 177.5(2) . . . . ?
N2 C4 C25 C16 -0.6(4) . . . . ?
N2 C5 C6 C7 -179.8(3) . . . . ?
N2 C5 C6 C16 0.5(4) . . . . ?
N2 C5 C18 C17 179.6(3) . . . . ?
C1 C2 C3 N1 -178.1(3) . . . . ?
C1 C2 C3 C11 0.1(4) . . . . ?
C1 C9 C10 C11 -0.1(5) . . . . ?
C2 C1 C9 C10 0.6(5) . . . . ?
C2 C3 C11 C10 0.4(4) . . . . ?
C2 C3 C11 C12 -178.9(2) . . . . ?
C3 N1 C4 N2 -177.9(2) . . . . ?
C3 N1 C4 C25 1.6(3) . . . . ?
C3 N1 C19 C20 -1.5(5) . . . . ?
C3 N1 C19 C24 176.7(2) . . . . ?
C3 C11 C12 C13 179.5(3) . . . . ?
C3 C11 C12 C25 0.3(4) . . . . ?
C4 N1 C3 C2 178.0(2) . . . . ?
C4 N1 C3 C11 -0.3(3) . . . . ?
C4 N1 C19 C20 -179.6(3) . . . . ?
C4 N1 C19 C24 -1.5(3) . . . . ?
C4 N2 C5 C6 -3.3(4) . . . . ?
C4 N2 C5 C18 176.2(3) . . . . ?
C4 N2 C24 C19 -1.5(3) . . . . ?
C4 N2 C24 C23 175.0(3) . . . . ?
C5 N2 C4 N1 -177.1(2) . . . . ?
C5 N2 C4 C25 3.4(4) . . . . ?
C5 N2 C24 C19 175.8(3) . . . . ?
C5 N2 C24 C23 -7.7(5) . . . . ?
C5 C6 C7 C8 -0.4(5) . . . . ?
C5 C6 C16 C15 -177.7(3) . . . . ?
C5 C6 C16 C25 2.2(4) . . . . ?
C6 C5 C18 C17 -0.9(5) . . . . ?
C6 C7 C8 C17 0.1(6) . . . . ?
C6 C16 C25 C4 -2.2(4) . . . . ?
C6 C16 C25 C12 179.9(2) . . . . ?
C7 C6 C16 C15 2.7(4) . . . . ?
C7 C6 C16 C25 -177.5(3) . . . . ?
C7 C8 C17 C18 -0.2(6) . . . . ?
C8 C17 C18 C5 0.6(6) . . . . ?
C9 C1 C2 C3 -0.6(5) . . . . ?
C9 C10 C11 C3 -0.4(4) . . . . ?
C9 C10 C11 C12 178.9(3) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C10 C11 C12 C25 -179.0(2) . . . . ?
C11 C12 C13 C14 -178.1(3) . . . . ?
C11 C12 C25 C4 0.9(3) . . . . ?
C11 C12 C25 C16 178.9(2) . . . . ?
C12 C13 C14 C15 -1.2(5) . . . . ?
C13 C12 C25 C4 -178.4(2) . . . . ?
C13 C12 C25 C16 -0.4(4) . . . . ?
C13 C14 C15 C16 0.5(5) . . . . ?
C14 C15 C16 C6 -179.9(3) . . . . ?
C14 C15 C16 C25 0.2(4) . . . . ?
C15 C16 C25 C4 177.7(2) . . . . ?
C15 C16 C25 C12 -0.3(4) . . . . ?
C16 C6 C7 C8 179.3(3) . . . . ?
C18 C5 C6 C7 0.8(4) . . . . ?
C18 C5 C6 C16 -178.9(3) . . . . ?
C19 N1 C3 C2 0.0(4) . . . . ?
C19 N1 C3 C11 -178.3(2) . . . . ?
C19 N1 C4 N2 0.6(3) . . . . ?
C19 N1 C4 C25 -180.0(2) . . . . ?
C19 C20 C21 C22 -1.2(6) . . . . ?
C20 C19 C24 N2 -179.7(3) . . . . ?
C20 C19 C24 C23 3.2(4) . . . . ?
C20 C21 C22 C23 2.5(7) . . . . ?
C21 C22 C23 C24 -0.8(6) . . . . ?
C22 C23 C24 N2 -178.1(3) . . . . ?
C22 C23 C24 C19 -2.0(5) . . . . ?
C24 N2 C4 N1 0.6(3) . . . . ?
C24 N2 C4 C25 -178.9(2) . . . . ?
C24 N2 C5 C6 179.7(2) . . . . ?
C24 N2 C5 C18 -0.8(4) . . . . ?
C24 C19 C20 C21 -1.6(5) . . . . ?
C25 C12 C13 C14 1.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
