# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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. 
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data_20180116a2_1
_database_code_depnum_ccdc_archive 'CCDC 2008533'
loop_
_audit_author_name
_audit_author_address
'Qiyao Li'
;the Hong Kong University of Science and Techonoly
China
;
_audit_update_record             
;
2020-06-08 deposited with the CCDC.	2020-10-19 downloaded from the CCDC.
;
_audit_creation_date             2018-01-16
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.12.08 svn.r3473 for OlexSys, GUI svn.r5433)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C32 H24 N, B F4'
_chemical_formula_sum            'C32 H24 B F4 N'
_chemical_formula_weight         509.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N B F'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.5860(2)
_cell_length_b                   15.1416(2)
_cell_length_c                   13.4977(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.2530(10)
_cell_angle_gamma                90
_cell_volume                     2551.70(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5556
_cell_measurement_temperature    199.99(10)
_cell_measurement_theta_max      73.2820
_cell_measurement_theta_min      2.9390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.931
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10212
_diffrn_reflns_point_group_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         64.999
_diffrn_reflns_theta_min         3.540
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):
  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  38.00   0.50    0.50    --    0.00  57.00-150.00   96
  2  ω     10.00  35.00   0.50    0.50    --    0.00 -77.00 150.00   50
  3  ω     57.00  86.00   0.50    0.50    --    0.00  57.00-150.00   58
  4  ω    -78.00  -4.00   0.50    0.50    --    0.00 -77.00 150.00  148
  5  ω     15.00 118.00   0.50    2.00    --   98.20 -82.00  90.00  206
  6  ω     18.00 115.00   0.50    2.00    --   98.20 -61.00-180.00  194
  7  ω     73.00 175.00   0.50    2.00    --   98.20  45.00  30.00  204
  8  ω     82.00 188.00   0.50    2.00    --   98.20  45.00 -60.00  212
  9  ω     27.00 115.00   0.50    2.00    --   98.20 -82.00 170.96  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0172213000
_diffrn_orient_matrix_UB_12      0.1003986000
_diffrn_orient_matrix_UB_13      0.0112805000
_diffrn_orient_matrix_UB_21      -0.0686772000
_diffrn_orient_matrix_UB_22      0.0148607000
_diffrn_orient_matrix_UB_23      -0.1014457000
_diffrn_orient_matrix_UB_31      -0.1010391000
_diffrn_orient_matrix_UB_32      0.0070433000
_diffrn_orient_matrix_UB_33      0.0531397000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3689
_reflns_number_total             4303
_reflns_odcompleteness_completeness 98.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4303
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.026
_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)+(0.0524P)²+0.8650P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1105
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26),
  C27(H27), C28(H28), C29(H29), C31(H31), C32(H32)
2.b Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C)
;
_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
N1 N 0.34399(9) 0.68283(8) 0.54035(9) 0.0290(3) Uani 1 1 d . . . . .
C1 C 0.49073(12) 0.77383(10) 0.50064(11) 0.0302(3) Uani 1 1 d . . . . .
C2 C 0.26944(12) 0.74635(10) 0.49547(11) 0.0306(3) Uani 1 1 d . . . . .
C3 C 0.30460(12) 0.82303(10) 0.46039(11) 0.0316(3) Uani 1 1 d . . . . .
C4 C 0.41712(12) 0.83809(10) 0.45902(11) 0.0315(3) Uani 1 1 d . . . . .
C5 C 0.22401(12) 0.88970(10) 0.41722(12) 0.0345(4) Uani 1 1 d . . . . .
C6 C 0.45304(11) 0.69880(10) 0.55211(11) 0.0288(3) Uani 1 1 d . . . . .
C7 C 0.30370(12) 0.60495(10) 0.57196(12) 0.0339(3) Uani 1 1 d . . . . .
H7 H 0.2301 0.5958 0.5614 0.041 Uiso 1 1 calc R . . . .
C8 C 0.15350(12) 0.72524(10) 0.49247(12) 0.0335(3) Uani 1 1 d . . . . .
C9 C 0.51899(12) 0.63812(10) 0.61276(11) 0.0319(3) Uani 1 1 d . . . . .
C10 C 0.59922(13) 0.78347(11) 0.48576(12) 0.0363(4) Uani 1 1 d . . . . .
H10 H 0.6482 0.7396 0.5080 0.044 Uiso 1 1 calc R . . . .
C11 C 0.63207(12) 0.65581(10) 0.65621(12) 0.0338(3) Uani 1 1 d . . . . .
C12 C 0.36711(13) 0.54088(10) 0.61794(12) 0.0371(4) Uani 1 1 d . . . . .
C13 C 0.47548(13) 0.56028(10) 0.64141(12) 0.0374(4) Uani 1 1 d . . . . .
H13 H 0.5198 0.5194 0.6776 0.045 Uiso 1 1 calc R . . . .
C14 C 0.09677(14) 0.75783(12) 0.56596(13) 0.0421(4) Uani 1 1 d . . . . .
H14 H 0.1311 0.7927 0.6170 0.051 Uiso 1 1 calc R . . . .
C15 C 0.45476(13) 0.91328(11) 0.41291(12) 0.0381(4) Uani 1 1 d . . . . .
H15 H 0.4067 0.9569 0.3878 0.046 Uiso 1 1 calc R . . . .
C16 C 0.66021(13) 0.73434(11) 0.70645(12) 0.0381(4) Uani 1 1 d . . . . .
H16 H 0.6102 0.7795 0.7071 0.046 Uiso 1 1 calc R . . . .
C17 C 0.56144(14) 0.92293(11) 0.40463(12) 0.0423(4) Uani 1 1 d . . . . .
H17 H 0.5859 0.9737 0.3760 0.051 Uiso 1 1 calc R . . . .
C18 C 0.76254(14) 0.74510(12) 0.75526(13) 0.0447(4) Uani 1 1 d . . . . .
H18 H 0.7815 0.7981 0.7875 0.054 Uiso 1 1 calc R . . . .
C19 C 0.63307(14) 0.85643(12) 0.43918(12) 0.0416(4) Uani 1 1 d . . . . .
H19 H 0.7049 0.8618 0.4304 0.050 Uiso 1 1 calc R . . . .
C20 C 0.17925(14) 0.88412(12) 0.31766(13) 0.0436(4) Uani 1 1 d . . . . .
H20 H 0.2008 0.8397 0.2771 0.052 Uiso 1 1 calc R . . . .
C21 C 0.70781(13) 0.58899(11) 0.65710(14) 0.0428(4) Uani 1 1 d . . . . .
H21 H 0.6900 0.5364 0.6235 0.051 Uiso 1 1 calc R . . . .
C22 C 0.10134(14) 0.67345(12) 0.41601(13) 0.0445(4) Uani 1 1 d . . . . .
H22 H 0.1385 0.6523 0.3656 0.053 Uiso 1 1 calc R . . . .
C23 C 0.19178(14) 0.95697(11) 0.47670(14) 0.0447(4) Uani 1 1 d . . . . .
H23 H 0.2213 0.9613 0.5433 0.054 Uiso 1 1 calc R . . . .
C24 C 0.83725(14) 0.67807(13) 0.75681(14) 0.0473(4) Uani 1 1 d . . . . .
H24 H 0.9057 0.6855 0.7908 0.057 Uiso 1 1 calc R . . . .
C25 C 0.80959(14) 0.60019(13) 0.70768(15) 0.0499(5) Uani 1 1 d . . . . .
H25 H 0.8595 0.5548 0.7085 0.060 Uiso 1 1 calc R . . . .
C26 C -0.01093(15) 0.73860(14) 0.56353(16) 0.0532(5) Uani 1 1 d . . . . .
H26 H -0.0491 0.7612 0.6125 0.064 Uiso 1 1 calc R . . . .
C27 C 0.07075(15) 1.01125(13) 0.33856(16) 0.0532(5) Uani 1 1 d . . . . .
H27 H 0.0190 1.0517 0.3124 0.064 Uiso 1 1 calc R . . . .
C28 C 0.10262(15) 0.94473(13) 0.27907(15) 0.0515(5) Uani 1 1 d . . . . .
H28 H 0.0725 0.9406 0.2127 0.062 Uiso 1 1 calc R . . . .
C29 C 0.11574(15) 1.01770(13) 0.43692(16) 0.0541(5) Uani 1 1 d . . . . .
H29 H 0.0949 1.0631 0.4768 0.065 Uiso 1 1 calc R . . . .
C30 C 0.32142(15) 0.45467(12) 0.64783(16) 0.0518(5) Uani 1 1 d . . . . .
H30A H 0.3268 0.4515 0.7193 0.078 Uiso 1 1 calc GR . . . .
H30B H 0.3607 0.4067 0.6234 0.078 Uiso 1 1 calc GR . . . .
H30C H 0.2476 0.4507 0.6199 0.078 Uiso 1 1 calc GR . . . .
C31 C -0.00609(15) 0.65357(14) 0.41542(16) 0.0549(5) Uani 1 1 d . . . . .
H31 H -0.0407 0.6181 0.3651 0.066 Uiso 1 1 calc R . . . .
C32 C -0.06202(15) 0.68603(14) 0.48879(16) 0.0572(5) Uani 1 1 d . . . . .
H32 H -0.1342 0.6725 0.4880 0.069 Uiso 1 1 calc R . . . .
F1 F 0.38357(12) 0.62537(7) 0.35133(7) 0.0691(4) Uani 1 1 d . . . . .
F2 F 0.34611(12) 0.73752(7) 0.24107(9) 0.0738(4) Uani 1 1 d . . . . .
F3 F 0.43422(12) 0.61754(9) 0.19867(10) 0.0789(4) Uani 1 1 d . . . . .
F4 F 0.26161(13) 0.60708(11) 0.21805(13) 0.0999(5) Uani 1 1 d . . . . .
B1 B 0.35679(18) 0.64790(13) 0.25275(14) 0.0418(5) 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
N1 C2 1.4243(19) . ?
N1 C6 1.3829(19) . ?
N1 C7 1.373(2) . ?
C1 C4 1.410(2) . ?
C1 C6 1.443(2) . ?
C1 C10 1.412(2) . ?
C2 C3 1.350(2) . ?
C2 C8 1.489(2) . ?
C3 C4 1.437(2) . ?
C3 C5 1.496(2) . ?
C4 C15 1.408(2) . ?
C5 C20 1.393(2) . ?
C5 C23 1.389(2) . ?
C6 C9 1.425(2) . ?
C7 H7 0.9300 . ?
C7 C12 1.356(2) . ?
C8 C14 1.384(2) . ?
C8 C22 1.393(2) . ?
C9 C11 1.493(2) . ?
C9 C13 1.375(2) . ?
C10 H10 0.9300 . ?
C10 C19 1.366(2) . ?
C11 C16 1.392(2) . ?
C11 C21 1.389(2) . ?
C12 C13 1.392(2) . ?
C12 C30 1.502(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C26 1.383(2) . ?
C15 H15 0.9300 . ?
C15 C17 1.369(2) . ?
C16 H16 0.9300 . ?
C16 C18 1.380(2) . ?
C17 H17 0.9300 . ?
C17 C19 1.392(3) . ?
C18 H18 0.9300 . ?
C18 C24 1.382(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C20 C28 1.385(2) . ?
C21 H21 0.9300 . ?
C21 C25 1.384(2) . ?
C22 H22 0.9300 . ?
C22 C31 1.384(3) . ?
C23 H23 0.9300 . ?
C23 C29 1.386(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.376(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C26 C32 1.379(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.379(3) . ?
C27 C29 1.380(3) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31 0.9300 . ?
C31 C32 1.376(3) . ?
C32 H32 0.9300 . ?
F1 B1 1.374(2) . ?
F2 B1 1.371(2) . ?
F3 B1 1.369(2) . ?
F4 B1 1.377(3) . ?

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
C6 N1 C2 121.45(12) . . ?
C7 N1 C2 117.57(12) . . ?
C7 N1 C6 120.98(13) . . ?
C4 C1 C6 119.71(14) . . ?
C4 C1 C10 118.06(14) . . ?
C10 C1 C6 122.16(14) . . ?
N1 C2 C8 117.21(13) . . ?
C3 C2 N1 120.17(13) . . ?
C3 C2 C8 122.59(13) . . ?
C2 C3 C4 120.56(14) . . ?
C2 C3 C5 118.75(14) . . ?
C4 C3 C5 120.59(13) . . ?
C1 C4 C3 118.97(14) . . ?
C15 C4 C1 119.54(14) . . ?
C15 C4 C3 121.41(14) . . ?
C20 C5 C3 120.44(14) . . ?
C23 C5 C3 120.19(14) . . ?
C23 C5 C20 119.36(15) . . ?
N1 C6 C1 117.67(13) . . ?
N1 C6 C9 116.79(13) . . ?
C9 C6 C1 125.53(13) . . ?
N1 C7 H7 118.7 . . ?
C12 C7 N1 122.53(14) . . ?
C12 C7 H7 118.7 . . ?
C14 C8 C2 119.75(14) . . ?
C14 C8 C22 119.61(15) . . ?
C22 C8 C2 120.63(15) . . ?
C6 C9 C11 124.53(14) . . ?
C13 C9 C6 119.35(14) . . ?
C13 C9 C11 115.90(14) . . ?
C1 C10 H10 119.6 . . ?
C19 C10 C1 120.82(16) . . ?
C19 C10 H10 119.6 . . ?
C16 C11 C9 121.04(14) . . ?
C21 C11 C9 119.45(14) . . ?
C21 C11 C16 119.06(15) . . ?
C7 C12 C13 117.15(15) . . ?
C7 C12 C30 121.44(15) . . ?
C13 C12 C30 121.30(15) . . ?
C9 C13 C12 122.02(14) . . ?
C9 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C8 C14 H14 120.0 . . ?
C26 C14 C8 120.05(17) . . ?
C26 C14 H14 120.0 . . ?
C4 C15 H15 119.6 . . ?
C17 C15 C4 120.70(15) . . ?
C17 C15 H15 119.6 . . ?
C11 C16 H16 120.1 . . ?
C18 C16 C11 119.86(16) . . ?
C18 C16 H16 120.1 . . ?
C15 C17 H17 120.1 . . ?
C15 C17 C19 119.72(15) . . ?
C19 C17 H17 120.1 . . ?
C16 C18 H18 119.6 . . ?
C16 C18 C24 120.85(17) . . ?
C24 C18 H18 119.6 . . ?
C10 C19 C17 120.85(16) . . ?
C10 C19 H19 119.6 . . ?
C17 C19 H19 119.6 . . ?
C5 C20 H20 120.0 . . ?
C28 C20 C5 120.03(17) . . ?
C28 C20 H20 120.0 . . ?
C11 C21 H21 119.8 . . ?
C25 C21 C11 120.43(17) . . ?
C25 C21 H21 119.8 . . ?
C8 C22 H22 120.2 . . ?
C31 C22 C8 119.70(17) . . ?
C31 C22 H22 120.2 . . ?
C5 C23 H23 120.0 . . ?
C29 C23 C5 120.04(17) . . ?
C29 C23 H23 120.0 . . ?
C18 C24 H24 120.3 . . ?
C25 C24 C18 119.46(16) . . ?
C25 C24 H24 120.3 . . ?
C21 C25 H25 119.8 . . ?
C24 C25 C21 120.32(17) . . ?
C24 C25 H25 119.8 . . ?
C14 C26 H26 119.9 . . ?
C32 C26 C14 120.27(18) . . ?
C32 C26 H26 119.9 . . ?
C28 C27 H27 120.1 . . ?
C28 C27 C29 119.86(17) . . ?
C29 C27 H27 120.1 . . ?
C20 C28 H28 119.8 . . ?
C27 C28 C20 120.34(18) . . ?
C27 C28 H28 119.8 . . ?
C23 C29 H29 119.8 . . ?
C27 C29 C23 120.36(18) . . ?
C27 C29 H29 119.8 . . ?
C12 C30 H30A 109.5 . . ?
C12 C30 H30B 109.5 . . ?
C12 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C22 C31 H31 119.8 . . ?
C32 C31 C22 120.41(18) . . ?
C32 C31 H31 119.8 . . ?
C26 C32 H32 120.0 . . ?
C31 C32 C26 119.94(17) . . ?
C31 C32 H32 120.0 . . ?
F1 B1 F4 108.34(17) . . ?
F2 B1 F1 111.45(15) . . ?
F2 B1 F4 109.69(17) . . ?
F3 B1 F1 109.21(16) . . ?
F3 B1 F2 109.71(16) . . ?
F3 B1 F4 108.38(17) . . ?

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 C2 C3 C4 6.0(2) . . . . ?
N1 C2 C3 C5 -177.71(13) . . . . ?
N1 C2 C8 C14 96.01(18) . . . . ?
N1 C2 C8 C22 -84.41(18) . . . . ?
N1 C6 C9 C11 -163.12(14) . . . . ?
N1 C6 C9 C13 11.3(2) . . . . ?
N1 C7 C12 C13 6.2(2) . . . . ?
N1 C7 C12 C30 -177.34(15) . . . . ?
C1 C4 C15 C17 2.6(2) . . . . ?
C1 C6 C9 C11 18.3(2) . . . . ?
C1 C6 C9 C13 -167.31(14) . . . . ?
C1 C10 C19 C17 -0.4(2) . . . . ?
C2 N1 C6 C1 -11.77(19) . . . . ?
C2 N1 C6 C9 169.55(13) . . . . ?
C2 N1 C7 C12 -178.26(14) . . . . ?
C2 C3 C4 C1 -3.9(2) . . . . ?
C2 C3 C4 C15 172.98(14) . . . . ?
C2 C3 C5 C20 -84.85(19) . . . . ?
C2 C3 C5 C23 94.06(19) . . . . ?
C2 C8 C14 C26 179.90(16) . . . . ?
C2 C8 C22 C31 179.08(16) . . . . ?
C3 C2 C8 C14 -82.1(2) . . . . ?
C3 C2 C8 C22 97.51(19) . . . . ?
C3 C4 C15 C17 -174.32(15) . . . . ?
C3 C5 C20 C28 178.28(16) . . . . ?
C3 C5 C23 C29 -178.88(16) . . . . ?
C4 C1 C6 N1 13.6(2) . . . . ?
C4 C1 C6 C9 -167.87(14) . . . . ?
C4 C1 C10 C19 5.0(2) . . . . ?
C4 C3 C5 C20 91.44(19) . . . . ?
C4 C3 C5 C23 -89.65(19) . . . . ?
C4 C15 C17 C19 2.1(2) . . . . ?
C5 C3 C4 C1 179.85(13) . . . . ?
C5 C3 C4 C15 -3.2(2) . . . . ?
C5 C20 C28 C27 0.5(3) . . . . ?
C5 C23 C29 C27 0.7(3) . . . . ?
C6 N1 C2 C3 2.1(2) . . . . ?
C6 N1 C2 C8 -176.02(13) . . . . ?
C6 N1 C7 C12 1.5(2) . . . . ?
C6 C1 C4 C3 -6.0(2) . . . . ?
C6 C1 C4 C15 177.06(13) . . . . ?
C6 C1 C10 C19 -178.18(14) . . . . ?
C6 C9 C11 C16 48.3(2) . . . . ?
C6 C9 C11 C21 -139.44(16) . . . . ?
C6 C9 C13 C12 -3.8(2) . . . . ?
C7 N1 C2 C3 -178.09(14) . . . . ?
C7 N1 C2 C8 3.79(19) . . . . ?
C7 N1 C6 C1 168.43(13) . . . . ?
C7 N1 C6 C9 -10.2(2) . . . . ?
C7 C12 C13 C9 -5.0(2) . . . . ?
C8 C2 C3 C4 -175.98(14) . . . . ?
C8 C2 C3 C5 0.3(2) . . . . ?
C8 C14 C26 C32 0.8(3) . . . . ?
C8 C22 C31 C32 1.2(3) . . . . ?
C9 C11 C16 C18 172.93(16) . . . . ?
C9 C11 C21 C25 -172.03(16) . . . . ?
C10 C1 C4 C3 170.94(13) . . . . ?
C10 C1 C4 C15 -6.0(2) . . . . ?
C10 C1 C6 N1 -163.20(13) . . . . ?
C10 C1 C6 C9 15.3(2) . . . . ?
C11 C9 C13 C12 171.02(15) . . . . ?
C11 C16 C18 C24 -1.4(3) . . . . ?
C11 C21 C25 C24 -0.7(3) . . . . ?
C13 C9 C11 C16 -126.22(17) . . . . ?
C13 C9 C11 C21 46.0(2) . . . . ?
C14 C8 C22 C31 -1.3(3) . . . . ?
C14 C26 C32 C31 -0.9(3) . . . . ?
C15 C17 C19 C10 -3.3(3) . . . . ?
C16 C11 C21 C25 0.4(3) . . . . ?
C16 C18 C24 C25 1.0(3) . . . . ?
C18 C24 C25 C21 0.0(3) . . . . ?
C20 C5 C23 C29 0.0(3) . . . . ?
C21 C11 C16 C18 0.7(2) . . . . ?
C22 C8 C14 C26 0.3(3) . . . . ?
C22 C31 C32 C26 -0.1(3) . . . . ?
C23 C5 C20 C28 -0.6(3) . . . . ?
C28 C27 C29 C23 -0.9(3) . . . . ?
C29 C27 C28 C20 0.3(3) . . . . ?
C30 C12 C13 C9 178.60(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.492
_oxdiff_exptl_absorpt_empirical_full_min 0.530
####################################################################### 
# 
# 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_qiyao12cult
_database_code_depnum_ccdc_archive 'CCDC 2035827'
loop_
_audit_author_name
_audit_author_address
'Qiyao Li'
;the Hong Kong University of Science and Techonoly
China
;
_audit_update_record             
;
2020-10-07 deposited with the CCDC.	2020-10-19 downloaded from the CCDC.
;
_audit_creation_date             2020-09-14
_audit_creation_method           
;
Olex2 1.2-beta
(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         '2(C H Cl3), B F4, C31 H20 N'
_chemical_formula_sum            'C33 H22 B Cl6 F4 N'
_chemical_formula_weight         732.02
_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 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.07767(20)
_cell_length_b                   21.6410(4)
_cell_length_c                   13.7711(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.8388(18)
_cell_angle_gamma                90
_cell_volume                     3231.14(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9312
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.82
_cell_measurement_theta_min      3.13
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.277
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.284
_exptl_crystal_size_min          0.253
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18004
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.500
_diffrn_reflns_theta_min         3.864
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4613
_reflns_number_total             5788
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.546
_refine_diff_density_min         -0.793
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         5788
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0695
_refine_ls_restrained_S_all      1.074
_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)+(0.0954P)²+6.5957P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1830
_refine_ls_wR_factor_ref         0.1947
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C39(H39), C40(H40)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14), C15(H15), C19(H19), C21(H21),
 C22(H22), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32),
  C33(H33), C35(H35), C36(H36), C37(H37), C38(H38)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Cl1 Cl 0.00558(12) 0.21650(5) 0.68966(9) 0.0515(3) Uani 1 1 d . . . . .
Cl0A Cl -0.50357(12) 0.24068(7) 0.62474(13) 0.0705(5) Uani 1 1 d . . . . .
Cl3 Cl -0.66637(13) 0.21512(7) 0.75733(15) 0.0752(5) Uani 1 1 d . . . . .
Cl4 Cl -0.17421(12) 0.19026(8) 0.51343(10) 0.0652(4) Uani 1 1 d . . . . .
Cl5 Cl -0.19787(15) 0.29909(6) 0.63062(17) 0.0862(6) Uani 1 1 d . . . . .
F1 F -0.44670(18) 0.43041(11) 1.22053(15) 0.0295(5) Uani 1 1 d . . . . .
Cl2 Cl -0.42283(18) 0.26462(9) 0.83249(17) 0.0946(6) Uani 1 1 d . . . . .
F3 F -0.2748(2) 0.45724(12) 1.33336(17) 0.0405(6) Uani 1 1 d . . . . .
N4 N -0.5475(3) 0.41494(13) 0.8089(2) 0.0178(6) Uani 1 1 d . . . . .
C5 C -0.5677(3) 0.41183(15) 0.6067(2) 0.0187(7) Uani 1 1 d . . . . .
F6 F -0.2752(2) 0.46573(17) 1.17308(18) 0.0588(9) Uani 1 1 d . . . . .
C7 C -0.6735(3) 0.39738(14) 0.6482(2) 0.0169(6) Uani 1 1 d . . . . .
C8 C -0.4456(3) 0.43353(15) 0.7750(2) 0.0176(6) Uani 1 1 d . . . . .
C9 C -0.6606(3) 0.39651(15) 0.7482(2) 0.0175(7) Uani 1 1 d . . . . .
C10 C -0.3475(3) 0.43152(16) 0.6269(3) 0.0213(7) Uani 1 1 d . . . . .
H10 H -0.268747 0.437991 0.668381 0.026 Uiso 1 1 calc R . . . .
C11 C -0.5752(3) 0.40982(16) 0.5035(2) 0.0207(7) Uani 1 1 d . . . . .
H11 H -0.652822 0.402690 0.460734 0.025 Uiso 1 1 calc R . . . .
C12 C -0.2376(3) 0.48934(16) 0.8236(2) 0.0203(7) Uani 1 1 d . . . . .
C13 C -0.3572(3) 0.42714(17) 0.5268(3) 0.0252(8) Uani 1 1 d . . . . .
H13 H -0.285241 0.430321 0.499579 0.030 Uiso 1 1 calc R . . . .
C14 C -0.4726(3) 0.41797(18) 0.4635(3) 0.0256(8) Uani 1 1 d . . . . .
H14 H -0.479505 0.417409 0.393545 0.031 Uiso 1 1 calc R . . . .
C15 C -0.3526(3) 0.45224(17) 0.9473(3) 0.0244(7) Uani 1 1 d . . . . .
H15 H -0.284039 0.465680 0.996042 0.029 Uiso 1 1 calc R . . . .
C16 C -0.7954(3) 0.38340(15) 0.5824(2) 0.0187(7) Uani 1 1 d . . . . .
C17 C -0.5547(3) 0.41212(16) 0.9077(3) 0.0222(7) Uani 1 1 d . . . . .
C18 C -0.7419(3) 0.38040(15) 0.8153(3) 0.0202(7) Uani 1 1 d . . . . .
C19 C -0.2534(3) 0.54157(16) 0.7628(3) 0.0229(7) Uani 1 1 d . . . . .
H19 H -0.334048 0.556525 0.736412 0.027 Uiso 1 1 calc R . . . .
C20 C -0.6770(3) 0.39017(15) 0.9119(3) 0.0220(7) Uani 1 1 d . . . . .
C21 C -0.1186(3) 0.46968(17) 0.8656(3) 0.0264(8) Uani 1 1 d . . . . .
H21 H -0.106698 0.435347 0.909476 0.032 Uiso 1 1 calc R . . . .
C22 C -0.4548(3) 0.42895(17) 0.9788(3) 0.0251(8) Uani 1 1 d . . . . .
H22 H -0.455371 0.424825 1.047386 0.030 Uiso 1 1 calc R . . . .
C23 C -0.4517(3) 0.42666(15) 0.6699(2) 0.0182(7) Uani 1 1 d . . . . .
C24 C -0.3459(3) 0.45683(16) 0.8480(2) 0.0200(7) Uani 1 1 d . . . . .
F25 F -0.2781(3) 0.37052(13) 1.2463(3) 0.0726(11) Uani 1 1 d . . . . .
C26 C -0.0336(3) 0.55073(18) 0.7799(3) 0.0303(8) Uani 1 1 d . . . . .
H26 H 0.035659 0.570846 0.763223 0.036 Uiso 1 1 calc R . . . .
C27 C -0.9281(4) 0.31821(18) 0.4659(3) 0.0295(8) Uani 1 1 d . . . . .
H27 H -0.941251 0.280925 0.428865 0.035 Uiso 1 1 calc R . . . .
C28 C -0.8624(3) 0.35743(15) 0.7975(3) 0.0233(7) Uani 1 1 d . . . . .
H28 H -0.907291 0.350207 0.731981 0.028 Uiso 1 1 calc R . . . .
C29 C -0.9138(4) 0.34559(17) 0.8797(3) 0.0293(8) Uani 1 1 d . . . . .
H29 H -0.995080 0.329371 0.869811 0.035 Uiso 1 1 calc R . . . .
C30 C -0.1521(3) 0.57170(17) 0.7409(3) 0.0267(8) Uani 1 1 d . . . . .
H30 H -0.163668 0.606946 0.698876 0.032 Uiso 1 1 calc R . . . .
C31 C -1.0027(3) 0.41500(19) 0.5107(3) 0.0357(9) Uani 1 1 d . . . . .
H31 H -1.066798 0.444811 0.504253 0.043 Uiso 1 1 calc R . . . .
C32 C -0.8896(3) 0.42653(17) 0.5746(3) 0.0275(8) Uani 1 1 d . . . . .
H32 H -0.877280 0.463583 0.612332 0.033 Uiso 1 1 calc R . . . .
C33 C -0.0169(3) 0.50031(19) 0.8433(3) 0.0321(9) Uani 1 1 d . . . . .
H33 H 0.064139 0.486564 0.871624 0.038 Uiso 1 1 calc R . . . .
B34 B -0.3171(4) 0.4305(2) 1.2435(3) 0.0224(8) Uani 1 1 d . . . . .
C35 C -0.8151(3) 0.32898(17) 0.5281(3) 0.0238(7) Uani 1 1 d . . . . .
H35 H -0.751152 0.299162 0.533627 0.029 Uiso 1 1 calc R . . . .
C36 C -1.0222(4) 0.36118(18) 0.4572(3) 0.0325(9) Uani 1 1 d . . . . .
H36 H -1.099693 0.353473 0.414534 0.039 Uiso 1 1 calc R . . . .
C37 C -0.7299(4) 0.37929(18) 0.9942(3) 0.0282(8) Uani 1 1 d . . . . .
H37 H -0.685635 0.387014 1.059736 0.034 Uiso 1 1 calc R . . . .
C38 C -0.8493(4) 0.35687(18) 0.9762(3) 0.0313(9) Uani 1 1 d . . . . .
H38 H -0.887983 0.349006 1.030474 0.038 Uiso 1 1 calc R . . . .
C39 C -0.1512(5) 0.2228(2) 0.6346(4) 0.0441(11) Uani 1 1 d . . . . .
H39 H -0.200287 0.198696 0.674874 0.053 Uiso 1 1 calc R . . . .
C40 C -0.5131(4) 0.2163(2) 0.7462(5) 0.0543(14) Uani 1 1 d . . . . .
H40 H -0.479455 0.173358 0.756502 0.065 Uiso 1 1 calc R . . . .


_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
Cl1 C39 1.752(5) . ?
Cl0A C40 1.778(7) . ?
Cl3 C40 1.736(5) . ?
Cl4 C39 1.781(5) . ?
Cl5 C39 1.727(5) . ?
F1 B34 1.405(4) . ?
Cl2 C40 1.737(5) . ?
F3 B34 1.360(4) . ?
N4 C8 1.368(4) . ?
N4 C9 1.414(4) . ?
N4 C17 1.381(4) . ?
C5 C7 1.440(5) . ?
C5 C11 1.407(5) . ?
C5 C23 1.432(5) . ?
F6 B34 1.387(5) . ?
C7 C9 1.356(5) . ?
C7 C16 1.494(4) . ?
C8 C23 1.443(5) . ?
C8 C24 1.425(5) . ?
C9 C18 1.458(5) . ?
C10 C13 1.364(5) . ?
C10 C23 1.405(5) . ?
C11 C14 1.373(5) . ?
C12 C19 1.396(5) . ?
C12 C21 1.393(5) . ?
C12 C24 1.487(5) . ?
C13 C14 1.406(5) . ?
C15 C22 1.387(5) . ?
C15 C24 1.389(5) . ?
C16 C32 1.388(5) . ?
C16 C35 1.388(5) . ?
C17 C20 1.447(5) . ?
C17 C22 1.368(5) . ?
C18 C20 1.393(5) . ?
C18 C28 1.398(5) . ?
C19 C30 1.384(5) . ?
C20 C37 1.398(5) . ?
C21 C33 1.395(5) . ?
F25 B34 1.365(5) . ?
C26 C30 1.389(5) . ?
C26 C33 1.386(6) . ?
C27 C35 1.384(5) . ?
C27 C36 1.384(6) . ?
C28 C29 1.391(5) . ?
C29 C38 1.396(6) . ?
C31 C32 1.398(5) . ?
C31 C36 1.371(6) . ?
C37 C38 1.382(6) . ?

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
C8 N4 C9 125.1(3) . . ?
C8 N4 C17 124.6(3) . . ?
C17 N4 C9 110.3(3) . . ?
C11 C5 C7 120.6(3) . . ?
C11 C5 C23 118.7(3) . . ?
C23 C5 C7 120.7(3) . . ?
C5 C7 C16 120.8(3) . . ?
C9 C7 C5 118.8(3) . . ?
C9 C7 C16 120.4(3) . . ?
N4 C8 C23 116.1(3) . . ?
N4 C8 C24 116.0(3) . . ?
C24 C8 C23 127.9(3) . . ?
N4 C9 C18 106.3(3) . . ?
C7 C9 N4 119.5(3) . . ?
C7 C9 C18 134.2(3) . . ?
C13 C10 C23 121.3(3) . . ?
C14 C11 C5 121.3(3) . . ?
C19 C12 C24 120.8(3) . . ?
C21 C12 C19 119.2(3) . . ?
C21 C12 C24 120.0(3) . . ?
C10 C13 C14 120.6(3) . . ?
C11 C14 C13 119.4(3) . . ?
C22 C15 C24 123.1(3) . . ?
C32 C16 C7 118.8(3) . . ?
C32 C16 C35 119.7(3) . . ?
C35 C16 C7 121.4(3) . . ?
N4 C17 C20 107.3(3) . . ?
C22 C17 N4 119.4(3) . . ?
C22 C17 C20 133.2(3) . . ?
C20 C18 C9 107.7(3) . . ?
C20 C18 C28 120.5(3) . . ?
C28 C18 C9 131.7(3) . . ?
C30 C19 C12 120.4(3) . . ?
C18 C20 C17 108.4(3) . . ?
C18 C20 C37 121.9(3) . . ?
C37 C20 C17 129.7(3) . . ?
C12 C21 C33 120.1(3) . . ?
C17 C22 C15 117.7(3) . . ?
C5 C23 C8 118.9(3) . . ?
C10 C23 C5 118.2(3) . . ?
C10 C23 C8 122.8(3) . . ?
C8 C24 C12 123.5(3) . . ?
C15 C24 C8 118.6(3) . . ?
C15 C24 C12 117.8(3) . . ?
C33 C26 C30 119.6(3) . . ?
C35 C27 C36 120.7(4) . . ?
C29 C28 C18 117.3(3) . . ?
C28 C29 C38 121.8(3) . . ?
C19 C30 C26 120.4(3) . . ?
C36 C31 C32 120.8(4) . . ?
C16 C32 C31 119.4(4) . . ?
C26 C33 C21 120.2(3) . . ?
F3 B34 F1 110.5(3) . . ?
F3 B34 F6 107.4(3) . . ?
F3 B34 F25 109.4(3) . . ?
F6 B34 F1 108.4(3) . . ?
F25 B34 F1 108.0(3) . . ?
F25 B34 F6 113.1(4) . . ?
C27 C35 C16 119.9(3) . . ?
C31 C36 C27 119.4(4) . . ?
C38 C37 C20 117.3(4) . . ?
C37 C38 C29 121.0(3) . . ?
Cl1 C39 Cl4 108.3(3) . . ?
Cl5 C39 Cl1 110.6(3) . . ?
Cl5 C39 Cl4 111.3(3) . . ?
Cl3 C40 Cl0A 109.6(3) . . ?
Cl3 C40 Cl2 112.6(3) . . ?
Cl2 C40 Cl0A 109.1(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
N4 C8 C23 C5 10.8(4) . . . . ?
N4 C8 C23 C10 -166.6(3) . . . . ?
N4 C8 C24 C12 -168.7(3) . . . . ?
N4 C8 C24 C15 7.5(5) . . . . ?
N4 C9 C18 C20 0.7(4) . . . . ?
N4 C9 C18 C28 -177.6(3) . . . . ?
N4 C17 C20 C18 -0.3(4) . . . . ?
N4 C17 C20 C37 179.9(4) . . . . ?
N4 C17 C22 C15 4.3(5) . . . . ?
C5 C7 C9 N4 5.5(5) . . . . ?
C5 C7 C9 C18 -175.2(3) . . . . ?
C5 C7 C16 C32 -108.4(4) . . . . ?
C5 C7 C16 C35 70.5(4) . . . . ?
C5 C11 C14 C13 1.4(6) . . . . ?
C7 C5 C11 C14 -174.0(3) . . . . ?
C7 C5 C23 C8 -6.7(5) . . . . ?
C7 C5 C23 C10 170.9(3) . . . . ?
C7 C9 C18 C20 -178.6(4) . . . . ?
C7 C9 C18 C28 3.1(6) . . . . ?
C7 C16 C32 C31 177.8(3) . . . . ?
C7 C16 C35 C27 -178.3(3) . . . . ?
C8 N4 C9 C7 -0.9(5) . . . . ?
C8 N4 C9 C18 179.7(3) . . . . ?
C8 N4 C17 C20 -179.8(3) . . . . ?
C8 N4 C17 C22 0.2(5) . . . . ?
C9 N4 C8 C23 -7.4(5) . . . . ?
C9 N4 C8 C24 173.1(3) . . . . ?
C9 N4 C17 C20 0.8(4) . . . . ?
C9 N4 C17 C22 -179.2(3) . . . . ?
C9 C7 C16 C32 71.8(4) . . . . ?
C9 C7 C16 C35 -109.3(4) . . . . ?
C9 C18 C20 C17 -0.2(4) . . . . ?
C9 C18 C20 C37 179.6(3) . . . . ?
C9 C18 C28 C29 178.7(3) . . . . ?
C10 C13 C14 C11 -3.8(6) . . . . ?
C11 C5 C7 C9 176.4(3) . . . . ?
C11 C5 C7 C16 -3.4(5) . . . . ?
C11 C5 C23 C8 175.2(3) . . . . ?
C11 C5 C23 C10 -7.2(5) . . . . ?
C12 C19 C30 C26 -0.7(6) . . . . ?
C12 C21 C33 C26 0.5(6) . . . . ?
C13 C10 C23 C5 5.1(5) . . . . ?
C13 C10 C23 C8 -177.5(3) . . . . ?
C16 C7 C9 N4 -174.7(3) . . . . ?
C16 C7 C9 C18 4.6(6) . . . . ?
C17 N4 C8 C23 173.3(3) . . . . ?
C17 N4 C8 C24 -6.2(5) . . . . ?
C17 N4 C9 C7 178.5(3) . . . . ?
C17 N4 C9 C18 -0.9(4) . . . . ?
C17 C20 C37 C38 -178.7(4) . . . . ?
C18 C20 C37 C38 1.5(5) . . . . ?
C18 C28 C29 C38 0.9(5) . . . . ?
C19 C12 C21 C33 -2.9(5) . . . . ?
C19 C12 C24 C8 55.9(5) . . . . ?
C19 C12 C24 C15 -120.4(4) . . . . ?
C20 C17 C22 C15 -175.7(4) . . . . ?
C20 C18 C28 C29 0.6(5) . . . . ?
C20 C37 C38 C29 0.0(6) . . . . ?
C21 C12 C19 C30 3.0(5) . . . . ?
C21 C12 C24 C8 -127.5(4) . . . . ?
C21 C12 C24 C15 56.2(5) . . . . ?
C22 C15 C24 C8 -3.5(5) . . . . ?
C22 C15 C24 C12 172.9(3) . . . . ?
C22 C17 C20 C18 179.6(4) . . . . ?
C22 C17 C20 C37 -0.2(7) . . . . ?
C23 C5 C7 C9 -1.7(5) . . . . ?
C23 C5 C7 C16 178.5(3) . . . . ?
C23 C5 C11 C14 4.1(5) . . . . ?
C23 C8 C24 C12 11.9(5) . . . . ?
C23 C8 C24 C15 -171.8(3) . . . . ?
C23 C10 C13 C14 0.4(6) . . . . ?
C24 C8 C23 C5 -169.8(3) . . . . ?
C24 C8 C23 C10 12.7(5) . . . . ?
C24 C12 C19 C30 179.7(3) . . . . ?
C24 C12 C21 C33 -179.6(3) . . . . ?
C24 C15 C22 C17 -2.6(6) . . . . ?
C28 C18 C20 C17 178.3(3) . . . . ?
C28 C18 C20 C37 -1.9(5) . . . . ?
C28 C29 C38 C37 -1.3(6) . . . . ?
C30 C26 C33 C21 1.8(6) . . . . ?
C32 C16 C35 C27 0.5(5) . . . . ?
C32 C31 C36 C27 -0.7(6) . . . . ?
C33 C26 C30 C19 -1.7(6) . . . . ?
C35 C16 C32 C31 -1.1(5) . . . . ?
C35 C27 C36 C31 0.2(6) . . . . ?
C36 C27 C35 C16 -0.1(6) . . . . ?
C36 C31 C32 C16 1.2(6) . . . . ?

_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_qiyao6cult
_database_code_depnum_ccdc_archive 'CCDC 2035839'
loop_
_audit_author_name
_audit_author_address
'Qiyao Li'
;the Hong Kong University of Science and Techonoly
China
;
_audit_update_record             
;
2020-10-07 deposited with the CCDC.	2020-10-19 downloaded from the CCDC.
;
_audit_creation_date             2018-06-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'F6 P, C31 H22 N'
_chemical_formula_sum            'C31 H22 F6 N P'
_chemical_formula_weight         553.46
_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 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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                   8.5484(5)
_cell_length_b                   11.4387(6)
_cell_length_c                   13.6080(9)
_cell_angle_alpha                103.553(5)
_cell_angle_beta                 90.551(5)
_cell_angle_gamma                98.266(5)
_cell_volume                     1278.83(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3063
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.1890
_cell_measurement_theta_min      5.2090
_shelx_estimated_absorpt_T_max   0.802
_shelx_estimated_absorpt_T_min   0.769
_exptl_absorpt_coefficient_mu    1.539
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7001
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.488
_diffrn_reflns_theta_min         4.021
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     30.00 113.00   1.00    1.00    --  107.97-111.00 -90.00   83
  2  ω    -65.00  41.00   1.00    1.00    --  -40.45  19.00  60.00  106
  3  ω   -116.00 -27.00   1.00    1.00    --  -40.45 -37.00-120.00   89
  4  ω    -65.00  20.00   1.00    1.00    --  -40.45  57.00-180.00   85
  5  ω     37.00  83.00   1.00    1.00    --   40.45-125.00 -60.00   46
  6  ω     35.00  73.00   1.00    1.00    --   40.45-125.00  90.00   38
  7  ω     79.00 175.00   1.00    1.00    --  107.97  61.00 120.00   96
  8  ω     90.00 178.00   1.00    1.00    --  107.97  77.00  60.00   88
  9  ω     29.00 139.00   1.00    1.00    --  107.97 -77.00 -30.00  110
 10  ω    101.00 148.00   1.00    1.00    --  107.97 111.00-180.00   47
 11  ω     82.00 172.00   1.00    1.00    --  107.97  77.00   0.00   90
 12  ω     57.00 149.00   1.00    1.00    --  107.97 178.00 -90.00   92
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0327583000
_diffrn_orient_matrix_UB_12      -0.1381957000
_diffrn_orient_matrix_UB_13      -0.0458049000
_diffrn_orient_matrix_UB_21      0.0554111000
_diffrn_orient_matrix_UB_22      -0.0229392000
_diffrn_orient_matrix_UB_23      0.1009711000
_diffrn_orient_matrix_UB_31      -0.1705499000
_diffrn_orient_matrix_UB_32      -0.0034074000
_diffrn_orient_matrix_UB_33      0.0359939000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3660
_reflns_number_total             4537
_reflns_odcompleteness_completeness 98.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.46
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         4537
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.024
_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)+(0.0570P)²+0.0480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1006
_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), C6(H6), C7(H7), C8(H8), C9(H9), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26),
  C28(H28), C29(H29), C30(H30), C31(H31), C32(H32)
;
_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
P1 P 0.15629(5) 0.43760(4) 0.21740(3) 0.02109(13) Uani 1 1 d . . . . .
F1 F 0.22044(12) 0.41100(9) 0.31933(8) 0.0282(2) Uani 1 1 d . . . . .
F2 F 0.09390(12) 0.46366(10) 0.11383(8) 0.0326(3) Uani 1 1 d . . . . .
F3 F 0.21740(12) 0.57954(9) 0.25941(8) 0.0311(3) Uani 1 1 d . . . . .
F4 F -0.01072(12) 0.45466(10) 0.26575(8) 0.0318(3) Uani 1 1 d . . . . .
F5 F 0.09603(14) 0.29517(10) 0.17384(9) 0.0383(3) Uani 1 1 d . . . . .
F6 F 0.32466(12) 0.42058(10) 0.16847(8) 0.0307(3) Uani 1 1 d . . . . .
N1 N 0.55581(16) 0.25665(12) 0.12273(11) 0.0200(3) Uani 1 1 d . . . . .
C2 C 0.6883(2) 0.34278(15) 0.12956(14) 0.0231(4) Uani 1 1 d . . . . .
H2 H 0.7562 0.3635 0.1887 0.028 Uiso 1 1 calc R . . . .
C3 C 0.7233(2) 0.39850(15) 0.05307(14) 0.0243(4) Uani 1 1 d . . . . .
H3 H 0.8202 0.4518 0.0555 0.029 Uiso 1 1 calc R . . . .
C4 C 0.6164(2) 0.37695(16) -0.02860(14) 0.0245(4) Uani 1 1 d . . . . .
H4 H 0.6342 0.4229 -0.0783 0.029 Uiso 1 1 calc R . . . .
C5 C 0.4836(2) 0.28892(15) -0.03857(13) 0.0205(4) Uani 1 1 d . . . . .
C6 C 0.2829(2) 0.04008(15) -0.07165(14) 0.0227(4) Uani 1 1 d . . . . .
H6 H 0.3106 0.0680 -0.1305 0.027 Uiso 1 1 calc R . . . .
C7 C 0.1774(2) -0.06489(16) -0.08017(14) 0.0257(4) Uani 1 1 d . . . . .
H7 H 0.1328 -0.1088 -0.1448 0.031 Uiso 1 1 calc R . . . .
C8 C 0.1354(2) -0.10745(15) 0.00570(14) 0.0269(4) Uani 1 1 d . . . . .
H8 H 0.0599 -0.1786 -0.0003 0.032 Uiso 1 1 calc R . . . .
C9 C 0.2033(2) -0.04640(15) 0.09855(14) 0.0263(4) Uani 1 1 d . . . . .
H9 H 0.1751 -0.0761 0.1566 0.032 Uiso 1 1 calc R . . . .
C10 C 0.3957(2) 0.12001(16) 0.20492(14) 0.0228(4) Uani 1 1 d . . . . .
C11 C 0.5170(2) 0.21187(15) 0.21066(13) 0.0219(4) Uani 1 1 d . . . . .
C12 C 0.46169(19) 0.21807(15) 0.03447(13) 0.0196(4) Uani 1 1 d . . . . .
C13 C 0.35019(19) 0.10635(15) 0.02298(13) 0.0199(4) Uani 1 1 d . . . . .
C14 C 0.3145(2) 0.05993(15) 0.10907(13) 0.0222(4) Uani 1 1 d . . . . .
C15 C 0.3647(2) 0.28311(15) -0.12082(13) 0.0217(4) Uani 1 1 d . . . . .
C16 C 0.4123(2) 0.28682(16) -0.21799(14) 0.0271(4) Uani 1 1 d . . . . .
H16 H 0.5204 0.2863 -0.2334 0.032 Uiso 1 1 calc R . . . .
C17 C 0.3021(2) 0.29126(18) -0.29245(15) 0.0339(5) Uani 1 1 d . . . . .
H17 H 0.3350 0.2933 -0.3586 0.041 Uiso 1 1 calc R . . . .
C18 C 0.1441(2) 0.29272(18) -0.27029(16) 0.0347(5) Uani 1 1 d . . . . .
H18 H 0.0687 0.2946 -0.3214 0.042 Uiso 1 1 calc R . . . .
C19 C 0.0968(2) 0.29142(16) -0.17348(15) 0.0296(4) Uani 1 1 d . . . . .
H19 H -0.0111 0.2938 -0.1581 0.036 Uiso 1 1 calc R . . . .
C20 C 0.2056(2) 0.28658(15) -0.09899(14) 0.0235(4) Uani 1 1 d . . . . .
H20 H 0.1720 0.2856 -0.0328 0.028 Uiso 1 1 calc R . . . .
C21 C 0.3459(2) 0.07962(16) 0.29842(14) 0.0250(4) Uani 1 1 d . . . . .
C22 C 0.2453(2) 0.14111(17) 0.36311(14) 0.0287(4) Uani 1 1 d . . . . .
H22 H 0.2086 0.2102 0.3489 0.034 Uiso 1 1 calc R . . . .
C23 C 0.1977(2) 0.10198(19) 0.44888(15) 0.0347(5) Uani 1 1 d . . . . .
H23 H 0.1289 0.1449 0.4933 0.042 Uiso 1 1 calc R . . . .
C24 C 0.2491(3) 0.0020(2) 0.47004(17) 0.0447(6) Uani 1 1 d . . . . .
H24 H 0.2165 -0.0240 0.5290 0.054 Uiso 1 1 calc R . . . .
C25 C 0.3482(3) -0.0605(2) 0.4056(2) 0.0576(7) Uani 1 1 d . . . . .
H25 H 0.3836 -0.1300 0.4198 0.069 Uiso 1 1 calc R . . . .
C26 C 0.3964(3) -0.0221(2) 0.31977(19) 0.0467(6) Uani 1 1 d . . . . .
H26 H 0.4644 -0.0658 0.2753 0.056 Uiso 1 1 calc R . . . .
C27 C 0.6132(2) 0.27220(16) 0.30541(13) 0.0244(4) Uani 1 1 d . . . . .
C28 C 0.5949(2) 0.38865(17) 0.35853(14) 0.0285(4) Uani 1 1 d . . . . .
H28 H 0.5191 0.4300 0.3349 0.034 Uiso 1 1 calc R . . . .
C29 C 0.6868(2) 0.44456(19) 0.44574(15) 0.0322(4) Uani 1 1 d . . . . .
H29 H 0.6724 0.5236 0.4823 0.039 Uiso 1 1 calc R . . . .
C30 C 0.7994(2) 0.38606(19) 0.48012(15) 0.0335(5) Uani 1 1 d . . . . .
H30 H 0.8634 0.4251 0.5394 0.040 Uiso 1 1 calc R . . . .
C31 C 0.8177(2) 0.2705(2) 0.42742(15) 0.0369(5) Uani 1 1 d . . . . .
H31 H 0.8952 0.2301 0.4506 0.044 Uiso 1 1 calc R . . . .
C32 C 0.7246(2) 0.21270(18) 0.34124(15) 0.0310(4) Uani 1 1 d . . . . .
H32 H 0.7367 0.1324 0.3065 0.037 Uiso 1 1 calc R . . . .


_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
P1 F1 1.5964(11) . ?
P1 F2 1.6087(11) . ?
P1 F3 1.5973(10) . ?
P1 F4 1.5960(11) . ?
P1 F5 1.6034(11) . ?
P1 F6 1.6097(11) . ?
N1 C2 1.377(2) . ?
N1 C11 1.432(2) . ?
N1 C12 1.384(2) . ?
C2 C3 1.357(2) . ?
C3 C4 1.385(2) . ?
C4 C5 1.388(2) . ?
C5 C12 1.420(2) . ?
C5 C15 1.488(2) . ?
C6 C7 1.375(2) . ?
C6 C13 1.402(2) . ?
C7 C8 1.399(3) . ?
C8 C9 1.370(3) . ?
C9 C14 1.409(2) . ?
C10 C11 1.353(2) . ?
C10 C14 1.443(2) . ?
C10 C21 1.498(2) . ?
C11 C27 1.488(2) . ?
C12 C13 1.456(2) . ?
C13 C14 1.414(2) . ?
C15 C16 1.396(2) . ?
C15 C20 1.399(2) . ?
C16 C17 1.391(3) . ?
C17 C18 1.388(3) . ?
C18 C19 1.385(3) . ?
C19 C20 1.385(3) . ?
C21 C22 1.381(3) . ?
C21 C26 1.387(3) . ?
C22 C23 1.389(3) . ?
C23 C24 1.371(3) . ?
C24 C25 1.375(3) . ?
C25 C26 1.387(3) . ?
C27 C28 1.390(3) . ?
C27 C32 1.393(3) . ?
C28 C29 1.384(3) . ?
C29 C30 1.385(3) . ?
C30 C31 1.380(3) . ?
C31 C32 1.383(3) . ?

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
F1 P1 F2 179.14(6) . . ?
F1 P1 F3 90.38(6) . . ?
F1 P1 F5 90.13(6) . . ?
F1 P1 F6 89.92(6) . . ?
F2 P1 F6 89.24(6) . . ?
F3 P1 F2 89.82(6) . . ?
F3 P1 F5 179.24(7) . . ?
F3 P1 F6 89.81(6) . . ?
F4 P1 F1 90.19(6) . . ?
F4 P1 F2 90.64(6) . . ?
F4 P1 F3 90.14(6) . . ?
F4 P1 F5 90.43(6) . . ?
F4 P1 F6 179.87(7) . . ?
F5 P1 F2 89.67(6) . . ?
F5 P1 F6 89.63(6) . . ?
C2 N1 C11 117.70(14) . . ?
C2 N1 C12 120.64(14) . . ?
C12 N1 C11 121.63(14) . . ?
C3 C2 N1 120.96(16) . . ?
C2 C3 C4 119.33(16) . . ?
C3 C4 C5 120.67(16) . . ?
C4 C5 C12 118.95(16) . . ?
C4 C5 C15 116.93(15) . . ?
C12 C5 C15 123.85(15) . . ?
C7 C6 C13 120.75(16) . . ?
C6 C7 C8 120.42(17) . . ?
C9 C8 C7 119.90(16) . . ?
C8 C9 C14 120.82(17) . . ?
C11 C10 C14 120.44(16) . . ?
C11 C10 C21 119.94(16) . . ?
C14 C10 C21 119.62(15) . . ?
N1 C11 C27 116.95(14) . . ?
C10 C11 N1 119.67(16) . . ?
C10 C11 C27 123.37(16) . . ?
N1 C12 C5 117.60(15) . . ?
N1 C12 C13 117.24(15) . . ?
C5 C12 C13 125.15(16) . . ?
C6 C13 C12 122.02(15) . . ?
C6 C13 C14 118.87(15) . . ?
C14 C13 C12 119.04(15) . . ?
C9 C14 C10 121.40(16) . . ?
C9 C14 C13 119.08(16) . . ?
C13 C14 C10 119.49(15) . . ?
C16 C15 C5 120.53(16) . . ?
C16 C15 C20 119.05(17) . . ?
C20 C15 C5 120.09(16) . . ?
C17 C16 C15 120.27(18) . . ?
C18 C17 C16 120.14(19) . . ?
C19 C18 C17 119.82(18) . . ?
C18 C19 C20 120.42(18) . . ?
C19 C20 C15 120.28(17) . . ?
C22 C21 C10 120.41(16) . . ?
C22 C21 C26 119.04(18) . . ?
C26 C21 C10 120.52(17) . . ?
C21 C22 C23 120.07(18) . . ?
C24 C23 C22 120.59(19) . . ?
C23 C24 C25 119.75(19) . . ?
C24 C25 C26 120.1(2) . . ?
C25 C26 C21 120.5(2) . . ?
C28 C27 C11 120.73(16) . . ?
C28 C27 C32 119.16(17) . . ?
C32 C27 C11 120.10(17) . . ?
C29 C28 C27 120.22(18) . . ?
C28 C29 C30 120.46(19) . . ?
C31 C30 C29 119.36(18) . . ?
C30 C31 C32 120.73(19) . . ?
C31 C32 C27 120.04(19) . . ?

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 C2 C3 C4 6.2(3) . . . . ?
N1 C11 C27 C28 72.6(2) . . . . ?
N1 C11 C27 C32 -106.63(19) . . . . ?
N1 C12 C13 C6 -161.26(16) . . . . ?
N1 C12 C13 C14 15.5(2) . . . . ?
C2 N1 C11 C10 -174.48(16) . . . . ?
C2 N1 C11 C27 6.5(2) . . . . ?
C2 N1 C12 C5 -14.5(2) . . . . ?
C2 N1 C12 C13 164.24(15) . . . . ?
C2 C3 C4 C5 -7.5(3) . . . . ?
C3 C4 C5 C12 -2.2(3) . . . . ?
C3 C4 C5 C15 172.14(16) . . . . ?
C4 C5 C12 N1 13.0(2) . . . . ?
C4 C5 C12 C13 -165.63(16) . . . . ?
C4 C5 C15 C16 46.2(2) . . . . ?
C4 C5 C15 C20 -127.19(18) . . . . ?
C5 C12 C13 C6 17.3(3) . . . . ?
C5 C12 C13 C14 -165.86(17) . . . . ?
C5 C15 C16 C17 -174.80(16) . . . . ?
C5 C15 C20 C19 174.61(15) . . . . ?
C6 C7 C8 C9 -2.0(3) . . . . ?
C6 C13 C14 C9 -4.8(3) . . . . ?
C6 C13 C14 C10 173.37(16) . . . . ?
C7 C6 C13 C12 -179.74(16) . . . . ?
C7 C6 C13 C14 3.4(3) . . . . ?
C7 C8 C9 C14 0.6(3) . . . . ?
C8 C9 C14 C10 -175.30(17) . . . . ?
C8 C9 C14 C13 2.8(3) . . . . ?
C10 C11 C27 C28 -106.4(2) . . . . ?
C10 C11 C27 C32 74.4(2) . . . . ?
C10 C21 C22 C23 179.02(17) . . . . ?
C10 C21 C26 C25 -179.0(2) . . . . ?
C11 N1 C2 C3 -173.13(16) . . . . ?
C11 N1 C12 C5 163.57(15) . . . . ?
C11 N1 C12 C13 -17.7(2) . . . . ?
C11 C10 C14 C9 171.02(17) . . . . ?
C11 C10 C14 C13 -7.1(3) . . . . ?
C11 C10 C21 C22 82.8(2) . . . . ?
C11 C10 C21 C26 -99.1(2) . . . . ?
C11 C27 C28 C29 -179.03(17) . . . . ?
C11 C27 C32 C31 177.82(17) . . . . ?
C12 N1 C2 C3 5.0(3) . . . . ?
C12 N1 C11 C10 7.4(2) . . . . ?
C12 N1 C11 C27 -171.57(15) . . . . ?
C12 C5 C15 C16 -139.79(18) . . . . ?
C12 C5 C15 C20 46.8(2) . . . . ?
C12 C13 C14 C9 178.28(16) . . . . ?
C12 C13 C14 C10 -3.5(2) . . . . ?
C13 C6 C7 C8 0.0(3) . . . . ?
C14 C10 C11 N1 5.4(3) . . . . ?
C14 C10 C11 C27 -175.63(16) . . . . ?
C14 C10 C21 C22 -97.6(2) . . . . ?
C14 C10 C21 C26 80.5(2) . . . . ?
C15 C5 C12 N1 -160.97(15) . . . . ?
C15 C5 C12 C13 20.4(3) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C16 C15 C20 C19 1.2(2) . . . . ?
C16 C17 C18 C19 0.9(3) . . . . ?
C17 C18 C19 C20 -1.1(3) . . . . ?
C18 C19 C20 C15 0.1(3) . . . . ?
C20 C15 C16 C17 -1.4(3) . . . . ?
C21 C10 C11 N1 -174.97(15) . . . . ?
C21 C10 C11 C27 4.0(3) . . . . ?
C21 C10 C14 C9 -8.6(3) . . . . ?
C21 C10 C14 C13 173.29(15) . . . . ?
C21 C22 C23 C24 -0.3(3) . . . . ?
C22 C21 C26 C25 -0.9(4) . . . . ?
C22 C23 C24 C25 -0.3(4) . . . . ?
C23 C24 C25 C26 0.3(4) . . . . ?
C24 C25 C26 C21 0.3(4) . . . . ?
C26 C21 C22 C23 0.9(3) . . . . ?
C27 C28 C29 C30 1.0(3) . . . . ?
C28 C27 C32 C31 -1.4(3) . . . . ?
C28 C29 C30 C31 -1.0(3) . . . . ?
C29 C30 C31 C32 -0.2(3) . . . . ?
C30 C31 C32 C27 1.4(3) . . . . ?
C32 C27 C28 C29 0.2(3) . . . . ?

_olex2_date_sample_data_collection 2018-05-09
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.250
_oxdiff_exptl_absorpt_empirical_full_min 0.838
####################################################################### 
# 
# 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_qiyao1cult
_database_code_depnum_ccdc_archive 'CCDC 2035826'
loop_
_audit_author_name
_audit_author_address
'Qiyao Li'
;the Hong Kong University of Science and Techonoly
China
;
_audit_update_record             
;
2020-10-07 deposited with the CCDC.	2020-10-19 downloaded from the CCDC.
;
_audit_creation_date             2020-09-14
_audit_creation_method           
;
Olex2 1.2-beta
(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         'C31 H22 N, B F4'
_chemical_formula_sum            'C31 H22 B F4 N'
_chemical_formula_weight         495.30
_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 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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                   8.4537(6)
_cell_length_b                   11.0248(9)
_cell_length_c                   13.8145(10)
_cell_angle_alpha                108.087(7)
_cell_angle_beta                 95.552(6)
_cell_angle_gamma                99.640(6)
_cell_volume                     1191.31(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2901
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.4880
_cell_measurement_theta_min      4.3090
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.884
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6420
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.494
_diffrn_reflns_theta_min         3.409
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00 144.00   1.00    8.00    --  110.57 -77.00 -90.00  112
  2  ω    -69.00  11.00   1.00    3.00    --  -40.57  57.00 -60.00   80
  3  ω    -72.00  38.00   1.00    3.00    --  -40.57  77.00  30.00  110
  4  ω   -116.00 -14.00   1.00    3.00    --  -40.57 -37.00 120.00  102
  5  ω     38.00  85.00   1.00    3.00    --   40.57-125.00-180.00   47
  6  ω     46.00 122.00   1.00    8.00    --  110.57-125.00 -90.00   76
  7  ω     30.00 113.00   1.00    8.00    --  110.57-104.00  86.00   83
  8  ω    108.00 137.00   1.00    8.00    --  110.57 -45.00 120.00   29
  9  ω     49.00 178.00   1.00    8.00    --  110.57  15.00  30.00  129
 10  ω    137.00 178.00   1.00    8.00    --  110.57  77.00 -90.00   41
 11  ω    108.00 177.00   1.00    8.00    --  110.57  77.00-120.00   69
 12  ω     77.00 123.00   1.00    8.00    --  110.57  77.00 -90.00   46
 13  ω     39.00  88.00   1.00    8.00    --  110.57 -45.00 120.00   49
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3381
_reflns_number_total             4214
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.007
_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)+(0.0510P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0957
_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:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C22(H22),
 C23(H23), C24(H24), C25(H25), C26(H26), C32(H32), C33(H33), C34(H34), C35(H35),
  C36(H36), C42(H42), C43(H43), C44(H44), C45(H45), C46(H46)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
N1 N 0.54780(14) 0.25976(11) 0.61794(9) 0.0176(3) Uani 1 1 d . . . . .
C1 C 0.50572(17) 0.21693(14) 0.70113(11) 0.0184(3) Uani 1 1 d . . . . .
C2 C 0.37714(18) 0.11759(14) 0.68488(11) 0.0188(3) Uani 1 1 d . . . . .
C3 C 0.29097(17) 0.04689(13) 0.58202(11) 0.0182(3) Uani 1 1 d . . . . .
C4 C 0.17162(18) -0.06829(14) 0.56056(11) 0.0201(3) Uani 1 1 d . . . . .
H4 H 0.141959 -0.097645 0.615363 0.024 Uiso 1 1 calc R . . . .
C5 C 0.09823(17) -0.13807(13) 0.46099(12) 0.0208(3) Uani 1 1 d . . . . .
H5 H 0.017174 -0.214804 0.447308 0.025 Uiso 1 1 calc R . . . .
C6 C 0.14248(18) -0.09648(13) 0.37981(11) 0.0202(3) Uani 1 1 d . . . . .
H6 H 0.094136 -0.146897 0.310890 0.024 Uiso 1 1 calc R . . . .
C7 C 0.25542(17) 0.01684(14) 0.39887(11) 0.0185(3) Uani 1 1 d . . . . .
H7 H 0.284605 0.044018 0.342979 0.022 Uiso 1 1 calc R . . . .
C8 C 0.32856(17) 0.09332(13) 0.50094(11) 0.0166(3) Uani 1 1 d . . . . .
C9 C 0.44737(16) 0.21367(13) 0.52292(11) 0.0166(3) Uani 1 1 d . . . . .
C10 C 0.47162(17) 0.28524(13) 0.45457(11) 0.0181(3) Uani 1 1 d . . . . .
C11 C 0.61301(17) 0.37902(14) 0.47425(11) 0.0199(3) Uani 1 1 d . . . . .
H11 H 0.632207 0.425644 0.427655 0.024 Uiso 1 1 calc R . . . .
C12 C 0.72692(17) 0.40542(13) 0.56157(12) 0.0202(3) Uani 1 1 d . . . . .
H12 H 0.829848 0.461076 0.570448 0.024 Uiso 1 1 calc R . . . .
C13 C 0.68909(17) 0.35060(13) 0.63400(12) 0.0195(3) Uani 1 1 d . . . . .
H13 H 0.761701 0.375501 0.697047 0.023 Uiso 1 1 calc R . . . .
C21 C 0.60223(18) 0.29099(14) 0.80520(11) 0.0206(3) Uani 1 1 d . . . . .
C22 C 0.5929(2) 0.42052(15) 0.85407(12) 0.0266(3) Uani 1 1 d . . . . .
H22 H 0.527662 0.462228 0.820267 0.032 Uiso 1 1 calc R . . . .
C23 C 0.6794(2) 0.48809(16) 0.95220(13) 0.0327(4) Uani 1 1 d . . . . .
H23 H 0.673313 0.576295 0.985245 0.039 Uiso 1 1 calc R . . . .
C24 C 0.7742(2) 0.42842(18) 1.00227(13) 0.0349(4) Uani 1 1 d . . . . .
H24 H 0.834166 0.475591 1.069099 0.042 Uiso 1 1 calc R . . . .
C25 C 0.7815(2) 0.29887(19) 0.95428(13) 0.0343(4) Uani 1 1 d . . . . .
H25 H 0.845177 0.257072 0.988978 0.041 Uiso 1 1 calc R . . . .
C26 C 0.6963(2) 0.23029(16) 0.85613(12) 0.0270(3) Uani 1 1 d . . . . .
H26 H 0.702054 0.141881 0.823622 0.032 Uiso 1 1 calc R . . . .
C31 C 0.32177(18) 0.08223(14) 0.77380(11) 0.0200(3) Uani 1 1 d . . . . .
C32 C 0.22438(19) 0.15441(15) 0.83326(12) 0.0239(3) Uani 1 1 d . . . . .
H32 H 0.194047 0.226239 0.817671 0.029 Uiso 1 1 calc R . . . .
C33 C 0.1716(2) 0.12125(16) 0.91548(13) 0.0307(4) Uani 1 1 d . . . . .
H33 H 0.104783 0.170613 0.955927 0.037 Uiso 1 1 calc R . . . .
C34 C 0.2152(2) 0.01690(17) 0.93930(13) 0.0329(4) Uani 1 1 d . . . . .
H34 H 0.179456 -0.004431 0.996239 0.039 Uiso 1 1 calc R . . . .
C35 C 0.3108(2) -0.05590(17) 0.87997(14) 0.0337(4) Uani 1 1 d . . . . .
H35 H 0.340394 -0.127850 0.895721 0.040 Uiso 1 1 calc R . . . .
C36 C 0.3637(2) -0.02363(16) 0.79690(13) 0.0289(4) Uani 1 1 d . . . . .
H36 H 0.428826 -0.074191 0.755816 0.035 Uiso 1 1 calc R . . . .
C41 C 0.34685(18) 0.27364(13) 0.36668(11) 0.0188(3) Uani 1 1 d . . . . .
C42 C 0.18468(18) 0.27301(13) 0.37995(12) 0.0208(3) Uani 1 1 d . . . . .
H42 H 0.152329 0.272590 0.443839 0.025 Uiso 1 1 calc R . . . .
C43 C 0.07082(19) 0.27299(15) 0.30057(13) 0.0264(3) Uani 1 1 d . . . . .
H43 H -0.039134 0.272175 0.310023 0.032 Uiso 1 1 calc R . . . .
C44 C 0.1179(2) 0.27416(16) 0.20742(13) 0.0312(4) Uani 1 1 d . . . . .
H44 H 0.039893 0.273574 0.152842 0.037 Uiso 1 1 calc R . . . .
C45 C 0.2782(2) 0.27618(15) 0.19379(12) 0.0287(4) Uani 1 1 d . . . . .
H45 H 0.309917 0.277090 0.129855 0.034 Uiso 1 1 calc R . . . .
C46 C 0.39276(19) 0.27688(14) 0.27296(12) 0.0228(3) Uani 1 1 d . . . . .
H46 H 0.502926 0.279582 0.263415 0.027 Uiso 1 1 calc R . . . .
F1 F 0.75919(13) 0.40630(9) 0.23542(8) 0.0372(3) Uani 1 1 d . . . . .
F2 F 0.70311(16) 0.60020(13) 0.32225(10) 0.0574(4) Uani 1 1 d . . . . .
F3 F 0.89844(11) 0.52699(10) 0.39452(7) 0.0304(2) Uani 1 1 d . . . . .
F4 F 0.93951(13) 0.59328(10) 0.25711(8) 0.0421(3) Uani 1 1 d . . . . .
B1 B 0.8251(2) 0.53187(17) 0.30121(13) 0.0215(3) 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
N1 C1 1.4248(19) . ?
N1 C9 1.3885(19) . ?
N1 C13 1.3744(18) . ?
C1 C2 1.354(2) . ?
C1 C21 1.490(2) . ?
C2 C3 1.442(2) . ?
C2 C31 1.492(2) . ?
C3 C4 1.413(2) . ?
C3 C8 1.410(2) . ?
C4 C5 1.374(2) . ?
C5 C6 1.397(2) . ?
C6 C7 1.374(2) . ?
C7 C8 1.414(2) . ?
C8 C9 1.4513(19) . ?
C9 C10 1.415(2) . ?
C10 C11 1.386(2) . ?
C10 C41 1.488(2) . ?
C11 C12 1.389(2) . ?
C12 C13 1.357(2) . ?
C21 C22 1.397(2) . ?
C21 C26 1.392(2) . ?
C22 C23 1.388(2) . ?
C23 C24 1.380(3) . ?
C24 C25 1.390(3) . ?
C25 C26 1.386(2) . ?
C31 C32 1.389(2) . ?
C31 C36 1.392(2) . ?
C32 C33 1.387(2) . ?
C33 C34 1.386(3) . ?
C34 C35 1.380(3) . ?
C35 C36 1.394(2) . ?
C41 C42 1.400(2) . ?
C41 C46 1.396(2) . ?
C42 C43 1.387(2) . ?
C43 C44 1.386(2) . ?
C44 C45 1.384(3) . ?
C45 C46 1.386(2) . ?
F1 B1 1.384(2) . ?
F2 B1 1.377(2) . ?
F3 B1 1.396(2) . ?
F4 B1 1.384(2) . ?

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
C9 N1 C1 121.24(12) . . ?
C13 N1 C1 118.65(12) . . ?
C13 N1 C9 120.10(12) . . ?
N1 C1 C21 117.12(12) . . ?
C2 C1 N1 120.04(13) . . ?
C2 C1 C21 122.74(13) . . ?
C1 C2 C3 120.35(14) . . ?
C1 C2 C31 120.08(13) . . ?
C3 C2 C31 119.56(13) . . ?
C4 C3 C2 121.60(13) . . ?
C8 C3 C2 118.97(13) . . ?
C8 C3 C4 119.43(13) . . ?
C5 C4 C3 120.44(13) . . ?
C4 C5 C6 120.17(13) . . ?
C7 C6 C5 120.51(14) . . ?
C6 C7 C8 120.58(13) . . ?
C3 C8 C7 118.66(13) . . ?
C3 C8 C9 119.72(13) . . ?
C7 C8 C9 121.52(13) . . ?
N1 C9 C8 116.85(13) . . ?
N1 C9 C10 117.76(12) . . ?
C10 C9 C8 125.36(13) . . ?
C9 C10 C41 123.46(13) . . ?
C11 C10 C9 119.02(13) . . ?
C11 C10 C41 117.31(13) . . ?
C10 C11 C12 120.53(14) . . ?
C13 C12 C11 119.08(13) . . ?
C12 C13 N1 121.31(14) . . ?
C22 C21 C1 119.90(14) . . ?
C26 C21 C1 120.44(13) . . ?
C26 C21 C22 119.60(15) . . ?
C23 C22 C21 119.76(16) . . ?
C24 C23 C22 120.67(16) . . ?
C23 C24 C25 119.57(15) . . ?
C26 C25 C24 120.41(16) . . ?
C25 C26 C21 119.98(15) . . ?
C32 C31 C2 119.59(13) . . ?
C32 C31 C36 119.44(14) . . ?
C36 C31 C2 120.96(14) . . ?
C33 C32 C31 119.78(15) . . ?
C34 C33 C32 120.75(16) . . ?
C35 C34 C33 119.76(16) . . ?
C34 C35 C36 119.87(16) . . ?
C31 C36 C35 120.39(15) . . ?
C42 C41 C10 120.47(13) . . ?
C46 C41 C10 120.30(14) . . ?
C46 C41 C42 118.90(14) . . ?
C43 C42 C41 120.53(15) . . ?
C44 C43 C42 119.84(15) . . ?
C45 C44 C43 120.13(15) . . ?
C44 C45 C46 120.33(15) . . ?
C45 C46 C41 120.25(15) . . ?
F1 B1 F3 109.37(13) . . ?
F1 B1 F4 109.95(13) . . ?
F2 B1 F1 109.59(14) . . ?
F2 B1 F3 107.51(13) . . ?
F2 B1 F4 110.77(15) . . ?
F4 B1 F3 109.61(13) . . ?

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 C1 C2 C3 5.5(2) . . . . ?
N1 C1 C2 C31 -173.28(12) . . . . ?
N1 C1 C21 C22 66.09(19) . . . . ?
N1 C1 C21 C26 -116.73(15) . . . . ?
N1 C9 C10 C11 13.99(19) . . . . ?
N1 C9 C10 C41 -160.59(13) . . . . ?
C1 N1 C9 C8 -19.03(18) . . . . ?
C1 N1 C9 C10 162.62(12) . . . . ?
C1 N1 C13 C12 -172.85(12) . . . . ?
C1 C2 C3 C4 170.94(13) . . . . ?
C1 C2 C3 C8 -8.3(2) . . . . ?
C1 C2 C31 C32 80.67(19) . . . . ?
C1 C2 C31 C36 -100.56(18) . . . . ?
C1 C21 C22 C23 178.20(14) . . . . ?
C1 C21 C26 C25 -177.93(15) . . . . ?
C2 C1 C21 C22 -110.23(17) . . . . ?
C2 C1 C21 C26 66.9(2) . . . . ?
C2 C3 C4 C5 -176.09(13) . . . . ?
C2 C3 C8 C7 173.84(12) . . . . ?
C2 C3 C8 C9 -2.66(19) . . . . ?
C2 C31 C32 C33 179.49(14) . . . . ?
C2 C31 C36 C35 -179.79(15) . . . . ?
C3 C2 C31 C32 -98.18(17) . . . . ?
C3 C2 C31 C36 80.59(19) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
C3 C8 C9 N1 15.90(19) . . . . ?
C3 C8 C9 C10 -165.90(13) . . . . ?
C4 C3 C8 C7 -5.38(19) . . . . ?
C4 C3 C8 C9 178.12(12) . . . . ?
C4 C5 C6 C7 -2.3(2) . . . . ?
C5 C6 C7 C8 -0.1(2) . . . . ?
C6 C7 C8 C3 3.9(2) . . . . ?
C6 C7 C8 C9 -179.64(13) . . . . ?
C7 C8 C9 N1 -160.51(12) . . . . ?
C7 C8 C9 C10 17.7(2) . . . . ?
C8 C3 C4 C5 3.1(2) . . . . ?
C8 C9 C10 C11 -164.20(13) . . . . ?
C8 C9 C10 C41 21.2(2) . . . . ?
C9 N1 C1 C2 8.6(2) . . . . ?
C9 N1 C1 C21 -167.80(12) . . . . ?
C9 N1 C13 C12 5.7(2) . . . . ?
C9 C10 C11 C12 -2.1(2) . . . . ?
C9 C10 C41 C42 45.0(2) . . . . ?
C9 C10 C41 C46 -141.71(14) . . . . ?
C10 C11 C12 C13 -8.3(2) . . . . ?
C10 C41 C42 C43 174.69(13) . . . . ?
C10 C41 C46 C45 -175.03(13) . . . . ?
C11 C10 C41 C42 -129.72(15) . . . . ?
C11 C10 C41 C46 43.61(19) . . . . ?
C11 C12 C13 N1 6.6(2) . . . . ?
C13 N1 C1 C2 -172.83(13) . . . . ?
C13 N1 C1 C21 10.75(19) . . . . ?
C13 N1 C9 C8 162.44(12) . . . . ?
C13 N1 C9 C10 -15.91(18) . . . . ?
C21 C1 C2 C3 -178.24(13) . . . . ?
C21 C1 C2 C31 2.9(2) . . . . ?
C21 C22 C23 C24 -0.2(3) . . . . ?
C22 C21 C26 C25 -0.7(2) . . . . ?
C22 C23 C24 C25 -0.8(3) . . . . ?
C23 C24 C25 C26 1.0(3) . . . . ?
C24 C25 C26 C21 -0.3(3) . . . . ?
C26 C21 C22 C23 1.0(2) . . . . ?
C31 C2 C3 C4 -10.2(2) . . . . ?
C31 C2 C3 C8 170.57(12) . . . . ?
C31 C32 C33 C34 0.2(3) . . . . ?
C32 C31 C36 C35 -1.0(2) . . . . ?
C32 C33 C34 C35 -0.7(3) . . . . ?
C33 C34 C35 C36 0.4(3) . . . . ?
C34 C35 C36 C31 0.5(3) . . . . ?
C36 C31 C32 C33 0.7(2) . . . . ?
C41 C10 C11 C12 172.85(13) . . . . ?
C41 C42 C43 C44 -0.3(2) . . . . ?
C42 C41 C46 C45 -1.6(2) . . . . ?
C42 C43 C44 C45 -0.4(2) . . . . ?
C43 C44 C45 C46 0.1(2) . . . . ?
C44 C45 C46 C41 0.9(2) . . . . ?
C46 C41 C42 C43 1.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_qiyao13cult
_database_code_depnum_ccdc_archive 'CCDC 2008534'
loop_
_audit_author_name
_audit_author_address
'Qiyao Li'
;the Hong Kong University of Science and Techonoly
China
;
_audit_update_record             
;
2020-06-08 deposited with the CCDC.	2020-10-19 downloaded from the CCDC.
;
_audit_creation_date             2019-08-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H22 N, B F4'
_chemical_formula_sum            'C32 H22 B F4 N'
_chemical_formula_weight         507.31
_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 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.62776(16)
_cell_length_b                   16.52398(16)
_cell_length_c                   18.67576(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4822.69(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10450
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.3040
_cell_measurement_theta_min      4.5340
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.884
_exptl_absorpt_coefficient_mu    0.846
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2096
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25969
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.496
_diffrn_reflns_theta_min         4.558
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     94.00 178.00   1.00    8.00    --  107.97 125.00-120.00   84
  2  ω    -67.00  31.00   1.00    4.00    --  -40.45  57.00 -90.00   98
  3  ω   -114.00 -15.00   1.00    4.00    --  -40.45 -57.00   0.00   99
  4  ω    -58.00  38.00   1.00    4.00    --  -40.45  77.00 120.00   96
  5  ω      1.00  77.00   1.00    4.00    --   40.45 -99.00 -60.00   76
  6  ω     79.00 178.00   1.00    8.00    --  107.97  61.00   0.00   99
  7  ω     35.00 117.00   1.00    8.00    --  107.97-125.00-120.00   82
  8  ω     74.00 164.00   1.00    8.00    --  107.97  77.00  60.00   90
  9  ω     79.00 178.00   1.00    8.00    --  107.97  77.00 -60.00   99
 10  ω     33.00 117.00   1.00    8.00    --  107.97-125.00  90.00   84
 11  ω     36.00 134.00   1.00    8.00    --  107.97 -77.00-120.00   98
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0094512000
_diffrn_orient_matrix_UB_12      0.0483850000
_diffrn_orient_matrix_UB_13      0.0701105000
_diffrn_orient_matrix_UB_21      0.0774226000
_diffrn_orient_matrix_UB_22      0.0526090000
_diffrn_orient_matrix_UB_23      -0.0211524000
_diffrn_orient_matrix_UB_31      -0.0602662000
_diffrn_orient_matrix_UB_32      0.0598672000
_diffrn_orient_matrix_UB_33      -0.0379821000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3787
_reflns_number_total             4353
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.46
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.020
_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)+(0.0630P)²+2.4306P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1153
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C16(H16), C17(H17), C18(H18),
 C19(H19), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C29(H29), C30(H30),
  C31(H31), C32(H32), C33(H33)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
N1 N 0.46667(8) 0.38261(8) 0.55570(7) 0.0205(3) Uani 1 1 d . . . . .
C2 C 0.41629(10) 0.43330(9) 0.51465(8) 0.0222(3) Uani 1 1 d . . . . .
C3 C 0.37359(10) 0.49673(10) 0.54735(9) 0.0238(3) Uani 1 1 d . . . . .
C4 C 0.37710(10) 0.50022(10) 0.62216(9) 0.0254(4) Uani 1 1 d . . . . .
H4 H 0.3461 0.5418 0.6458 0.030 Uiso 1 1 calc R . . . .
C5 C 0.42348(10) 0.44610(10) 0.66346(9) 0.0240(3) Uani 1 1 d . . . . .
C6 C 0.57464(11) 0.35210(11) 0.72997(9) 0.0267(4) Uani 1 1 d . . . . .
H6 H 0.5512 0.3944 0.7583 0.032 Uiso 1 1 calc R . . . .
C7 C 0.63846(11) 0.30442(11) 0.75740(9) 0.0316(4) Uani 1 1 d . . . . .
H7 H 0.6595 0.3149 0.8042 0.038 Uiso 1 1 calc R . . . .
C8 C 0.67316(11) 0.24062(11) 0.71763(10) 0.0310(4) Uani 1 1 d . . . . .
H8 H 0.7153 0.2063 0.7382 0.037 Uiso 1 1 calc R . . . .
C9 C 0.64595(11) 0.22798(10) 0.64870(9) 0.0272(4) Uani 1 1 d . . . . .
H9 H 0.6703 0.1853 0.6214 0.033 Uiso 1 1 calc R . . . .
C10 C 0.55866(10) 0.26739(9) 0.54350(8) 0.0216(3) Uani 1 1 d . . . . .
C11 C 0.50444(10) 0.32148(9) 0.51320(8) 0.0214(3) Uani 1 1 d . . . . .
C12 C 0.47752(10) 0.38904(9) 0.62862(8) 0.0216(3) Uani 1 1 d . . . . .
C13 C 0.54330(10) 0.33899(10) 0.65983(9) 0.0229(3) Uani 1 1 d . . . . .
C14 C 0.58223(10) 0.27741(10) 0.61775(8) 0.0229(3) Uani 1 1 d . . . . .
C15 C 0.42003(10) 0.40401(10) 0.44154(9) 0.0255(3) Uani 1 1 d . . . . .
C16 C 0.38105(12) 0.43180(11) 0.37864(10) 0.0307(4) Uani 1 1 d . . . . .
H16 H 0.3436 0.4771 0.3794 0.037 Uiso 1 1 calc R . . . .
C17 C 0.39864(12) 0.39140(12) 0.31536(9) 0.0341(4) Uani 1 1 d . . . . .
H17 H 0.3728 0.4092 0.2721 0.041 Uiso 1 1 calc R . . . .
C18 C 0.45400(13) 0.32472(11) 0.31406(9) 0.0331(4) Uani 1 1 d . . . . .
H18 H 0.4657 0.2985 0.2698 0.040 Uiso 1 1 calc R . . . .
C19 C 0.49192(12) 0.29636(11) 0.37625(9) 0.0294(4) Uani 1 1 d . . . . .
H19 H 0.5292 0.2510 0.3749 0.035 Uiso 1 1 calc R . . . .
C20 C 0.47465(10) 0.33519(10) 0.44051(9) 0.0244(3) Uani 1 1 d . . . . .
C21 C 0.31920(11) 0.55406(10) 0.50503(9) 0.0299(4) Uani 1 1 d . . . . .
H21A H 0.2994 0.5979 0.5362 0.045 Uiso 1 1 calc GR . . . .
H21B H 0.2697 0.5250 0.4856 0.045 Uiso 1 1 calc GR . . . .
H21C H 0.3529 0.5767 0.4656 0.045 Uiso 1 1 calc GR . . . .
C22 C 0.40779(10) 0.44525(10) 0.74210(9) 0.0255(4) Uani 1 1 d . . . . .
C23 C 0.41917(11) 0.51443(11) 0.78368(9) 0.0301(4) Uani 1 1 d . . . . .
H23 H 0.4396 0.5629 0.7622 0.036 Uiso 1 1 calc R . . . .
C24 C 0.40082(12) 0.51275(12) 0.85611(10) 0.0332(4) Uani 1 1 d . . . . .
H24 H 0.4097 0.5598 0.8843 0.040 Uiso 1 1 calc R . . . .
C25 C 0.36963(11) 0.44282(13) 0.88783(10) 0.0340(4) Uani 1 1 d . . . . .
H25 H 0.3577 0.4420 0.9377 0.041 Uiso 1 1 calc R . . . .
C26 C 0.35588(12) 0.37413(12) 0.84668(10) 0.0350(4) Uani 1 1 d . . . . .
H26 H 0.3336 0.3265 0.8681 0.042 Uiso 1 1 calc R . . . .
C27 C 0.37488(11) 0.37525(11) 0.77393(10) 0.0311(4) Uani 1 1 d . . . . .
H27 H 0.3655 0.3282 0.7457 0.037 Uiso 1 1 calc R . . . .
C28 C 0.59666(10) 0.20115(9) 0.49984(8) 0.0215(3) Uani 1 1 d . . . . .
C29 C 0.54837(10) 0.13288(10) 0.48339(8) 0.0236(3) Uani 1 1 d . . . . .
H29 H 0.4908 0.1289 0.4993 0.028 Uiso 1 1 calc R . . . .
C30 C 0.58438(11) 0.07057(10) 0.44364(8) 0.0255(4) Uani 1 1 d . . . . .
H30 H 0.5516 0.0236 0.4331 0.031 Uiso 1 1 calc R . . . .
C31 C 0.66795(11) 0.07658(10) 0.41918(9) 0.0262(4) Uani 1 1 d . . . . .
H31 H 0.6922 0.0340 0.3916 0.031 Uiso 1 1 calc R . . . .
C32 C 0.71605(11) 0.14470(10) 0.43497(9) 0.0272(4) Uani 1 1 d . . . . .
H32 H 0.7732 0.1489 0.4179 0.033 Uiso 1 1 calc R . . . .
C33 C 0.68102(10) 0.20686(10) 0.47562(9) 0.0249(3) Uani 1 1 d . . . . .
H33 H 0.7144 0.2532 0.4869 0.030 Uiso 1 1 calc R . . . .
F1 F 0.65319(7) 0.83433(7) 0.45494(5) 0.0377(3) Uani 1 1 d . . . . .
F2 F 0.57326(8) 0.87921(8) 0.36180(6) 0.0491(3) Uani 1 1 d . . . . .
F3 F 0.71704(8) 0.86742(8) 0.34960(6) 0.0500(3) Uani 1 1 d . . . . .
F4 F 0.63381(8) 0.75601(7) 0.35707(7) 0.0465(3) Uani 1 1 d . . . . .
B1 B 0.64446(12) 0.83460(12) 0.38085(10) 0.0256(4) 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
N1 C2 1.382(2) . ?
N1 C11 1.414(2) . ?
N1 C12 1.377(2) . ?
C2 C3 1.385(2) . ?
C2 C15 1.450(2) . ?
C3 C4 1.399(2) . ?
C3 C21 1.498(2) . ?
C4 C5 1.386(2) . ?
C5 C12 1.423(2) . ?
C5 C22 1.489(2) . ?
C6 C7 1.370(3) . ?
C6 C13 1.415(2) . ?
C7 C8 1.399(3) . ?
C8 C9 1.372(2) . ?
C9 C14 1.412(2) . ?
C10 C11 1.355(2) . ?
C10 C14 1.444(2) . ?
C10 C28 1.489(2) . ?
C11 C20 1.453(2) . ?
C12 C13 1.442(2) . ?
C13 C14 1.422(2) . ?
C15 C16 1.401(2) . ?
C15 C20 1.422(2) . ?
C16 C17 1.385(3) . ?
C17 C18 1.401(3) . ?
C18 C19 1.385(2) . ?
C19 C20 1.387(2) . ?
C22 C23 1.393(2) . ?
C22 C27 1.398(2) . ?
C23 C24 1.383(3) . ?
C24 C25 1.387(3) . ?
C25 C26 1.388(3) . ?
C26 C27 1.391(3) . ?
C28 C29 1.391(2) . ?
C28 C33 1.397(2) . ?
C29 C30 1.389(2) . ?
C30 C31 1.387(2) . ?
C31 C32 1.385(3) . ?
C32 C33 1.390(2) . ?
F1 B1 1.390(2) . ?
F2 B1 1.382(2) . ?
F3 B1 1.386(2) . ?
F4 B1 1.382(2) . ?

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 C11 111.07(13) . . ?
C12 N1 C2 124.91(13) . . ?
C12 N1 C11 124.00(13) . . ?
N1 C2 C3 119.27(14) . . ?
N1 C2 C15 107.29(13) . . ?
C3 C2 C15 133.43(15) . . ?
C2 C3 C4 116.91(15) . . ?
C2 C3 C21 121.30(15) . . ?
C4 C3 C21 121.53(15) . . ?
C5 C4 C3 123.35(15) . . ?
C4 C5 C12 118.91(15) . . ?
C4 C5 C22 117.96(15) . . ?
C12 C5 C22 122.85(15) . . ?
C7 C6 C13 120.66(16) . . ?
C6 C7 C8 121.12(16) . . ?
C9 C8 C7 119.53(16) . . ?
C8 C9 C14 120.98(16) . . ?
C11 C10 C14 119.00(14) . . ?
C11 C10 C28 120.37(14) . . ?
C14 C10 C28 120.56(14) . . ?
N1 C11 C20 106.23(13) . . ?
C10 C11 N1 119.85(14) . . ?
C10 C11 C20 133.89(15) . . ?
N1 C12 C5 115.49(14) . . ?
N1 C12 C13 116.31(14) . . ?
C5 C12 C13 128.17(15) . . ?
C6 C13 C12 122.20(15) . . ?
C6 C13 C14 118.23(15) . . ?
C14 C13 C12 119.45(14) . . ?
C9 C14 C10 120.44(15) . . ?
C9 C14 C13 119.30(15) . . ?
C13 C14 C10 120.23(15) . . ?
C16 C15 C2 131.52(16) . . ?
C16 C15 C20 120.79(16) . . ?
C20 C15 C2 107.69(14) . . ?
C17 C16 C15 118.12(17) . . ?
C16 C17 C18 121.09(16) . . ?
C19 C18 C17 121.03(16) . . ?
C18 C19 C20 119.05(17) . . ?
C15 C20 C11 107.72(14) . . ?
C19 C20 C11 132.36(16) . . ?
C19 C20 C15 119.89(15) . . ?
C23 C22 C5 121.39(16) . . ?
C23 C22 C27 119.25(16) . . ?
C27 C22 C5 119.19(15) . . ?
C24 C23 C22 120.14(17) . . ?
C23 C24 C25 120.49(17) . . ?
C24 C25 C26 119.96(17) . . ?
C25 C26 C27 119.81(18) . . ?
C26 C27 C22 120.32(17) . . ?
C29 C28 C10 120.05(14) . . ?
C29 C28 C33 119.67(14) . . ?
C33 C28 C10 120.27(14) . . ?
C30 C29 C28 119.96(15) . . ?
C31 C30 C29 120.30(15) . . ?
C32 C31 C30 119.93(15) . . ?
C31 C32 C33 120.21(15) . . ?
C32 C33 C28 119.92(15) . . ?
F2 B1 F1 109.70(14) . . ?
F2 B1 F3 109.98(16) . . ?
F2 B1 F4 108.75(15) . . ?
F3 B1 F1 109.88(14) . . ?
F4 B1 F1 109.18(15) . . ?
F4 B1 F3 109.32(15) . . ?

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 C2 C3 C4 -6.7(2) . . . . ?
N1 C2 C3 C21 179.11(14) . . . . ?
N1 C2 C15 C16 179.47(17) . . . . ?
N1 C2 C15 C20 -0.57(17) . . . . ?
N1 C11 C20 C15 0.02(17) . . . . ?
N1 C11 C20 C19 177.99(18) . . . . ?
N1 C12 C13 C6 165.40(14) . . . . ?
N1 C12 C13 C14 -10.6(2) . . . . ?
C2 N1 C11 C10 177.70(14) . . . . ?
C2 N1 C11 C20 -0.39(17) . . . . ?
C2 N1 C12 C5 8.3(2) . . . . ?
C2 N1 C12 C13 -170.14(14) . . . . ?
C2 C3 C4 C5 2.8(2) . . . . ?
C2 C15 C16 C17 178.64(17) . . . . ?
C2 C15 C20 C11 0.33(18) . . . . ?
C2 C15 C20 C19 -177.93(15) . . . . ?
C3 C2 C15 C16 0.7(3) . . . . ?
C3 C2 C15 C20 -179.39(17) . . . . ?
C3 C4 C5 C12 6.7(2) . . . . ?
C3 C4 C5 C22 -167.41(15) . . . . ?
C4 C5 C12 N1 -11.8(2) . . . . ?
C4 C5 C12 C13 166.45(15) . . . . ?
C4 C5 C22 C23 -58.3(2) . . . . ?
C4 C5 C22 C27 116.94(18) . . . . ?
C5 C12 C13 C6 -12.8(3) . . . . ?
C5 C12 C13 C14 171.16(15) . . . . ?
C5 C22 C23 C24 177.41(16) . . . . ?
C5 C22 C27 C26 -176.99(16) . . . . ?
C6 C7 C8 C9 3.3(3) . . . . ?
C6 C13 C14 C9 4.5(2) . . . . ?
C6 C13 C14 C10 -173.51(14) . . . . ?
C7 C6 C13 C12 -178.62(16) . . . . ?
C7 C6 C13 C14 -2.6(2) . . . . ?
C7 C8 C9 C14 -1.3(3) . . . . ?
C8 C9 C14 C10 175.37(16) . . . . ?
C8 C9 C14 C13 -2.7(2) . . . . ?
C10 C11 C20 C15 -177.68(17) . . . . ?
C10 C11 C20 C19 0.3(3) . . . . ?
C10 C28 C29 C30 -178.96(14) . . . . ?
C10 C28 C33 C32 179.92(15) . . . . ?
C11 N1 C2 C3 179.62(13) . . . . ?
C11 N1 C2 C15 0.60(17) . . . . ?
C11 N1 C12 C5 -170.05(14) . . . . ?
C11 N1 C12 C13 11.5(2) . . . . ?
C11 C10 C14 C9 -172.65(15) . . . . ?
C11 C10 C14 C13 5.4(2) . . . . ?
C11 C10 C28 C29 -78.4(2) . . . . ?
C11 C10 C28 C33 102.03(18) . . . . ?
C12 N1 C2 C3 1.0(2) . . . . ?
C12 N1 C2 C15 -177.97(14) . . . . ?
C12 N1 C11 C10 -3.7(2) . . . . ?
C12 N1 C11 C20 178.20(14) . . . . ?
C12 C5 C22 C23 127.85(18) . . . . ?
C12 C5 C22 C27 -57.0(2) . . . . ?
C12 C13 C14 C9 -179.34(14) . . . . ?
C12 C13 C14 C10 2.6(2) . . . . ?
C13 C6 C7 C8 -1.3(3) . . . . ?
C14 C10 C11 N1 -5.0(2) . . . . ?
C14 C10 C11 C20 172.45(16) . . . . ?
C14 C10 C28 C29 104.65(18) . . . . ?
C14 C10 C28 C33 -74.9(2) . . . . ?
C15 C2 C3 C4 172.01(17) . . . . ?
C15 C2 C3 C21 -2.2(3) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C15 C20 C11 -179.70(15) . . . . ?
C16 C15 C20 C19 2.0(2) . . . . ?
C16 C17 C18 C19 0.9(3) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C18 C19 C20 C11 -178.98(17) . . . . ?
C18 C19 C20 C15 -1.2(3) . . . . ?
C20 C15 C16 C17 -1.3(3) . . . . ?
C21 C3 C4 C5 176.99(15) . . . . ?
C22 C5 C12 N1 162.03(14) . . . . ?
C22 C5 C12 C13 -19.7(2) . . . . ?
C22 C23 C24 C25 -1.1(3) . . . . ?
C23 C22 C27 C26 -1.7(3) . . . . ?
C23 C24 C25 C26 -0.6(3) . . . . ?
C24 C25 C26 C27 1.1(3) . . . . ?
C25 C26 C27 C22 0.0(3) . . . . ?
C27 C22 C23 C24 2.2(3) . . . . ?
C28 C10 C11 N1 178.02(13) . . . . ?
C28 C10 C11 C20 -4.5(3) . . . . ?
C28 C10 C14 C9 4.3(2) . . . . ?
C28 C10 C14 C13 -177.68(14) . . . . ?
C28 C29 C30 C31 -1.1(2) . . . . ?
C29 C28 C33 C32 0.4(2) . . . . ?
C29 C30 C31 C32 0.6(2) . . . . ?
C30 C31 C32 C33 0.4(2) . . . . ?
C31 C32 C33 C28 -0.9(2) . . . . ?
C33 C28 C29 C30 0.6(2) . . . . ?

_olex2_date_sample_data_collection 2018-07-30
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.172
_oxdiff_exptl_absorpt_empirical_full_min 0.846
