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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_nap-cor-yl
_database_code_depnum_ccdc_archive 'CCDC 2075923'
loop_
_audit_author_name
_audit_author_address
'Jun Xu'
;Tianjin University
China
;
_audit_update_record             
;
2021-04-07 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_audit_creation_date             2021-04-01
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H23 N O2'
_chemical_formula_sum            'C36 H23 N O2'
_chemical_formula_weight         501.55
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   17.1874(5)
_cell_length_b                   7.5058(3)
_cell_length_c                   37.0743(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4782.8(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4601
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.2110
_cell_measurement_theta_min      3.4950
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.823
_exptl_absorpt_coefficient_mu    0.674
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2096
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            15372
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.522
_diffrn_reflns_theta_min         3.507
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00  29.00   0.50    1.75    --  -47.00  19.00-120.00  180
  2  ω     56.00 119.00   0.50    1.75    --   47.00  57.00-180.00  126
  3  ω     93.00 153.00   0.50    7.00    --  107.61  37.00  30.00  120
  4  ω     76.00 109.00   0.50    7.00    --  107.61 -99.00-150.00   66
  5  ω     35.00 104.00   0.50    7.00    --  107.61-125.00-177.00  138
  6  ω     38.00 102.00   0.50    7.00    --  107.61 -99.00   0.00  128
  7  ω     63.00  97.00   0.50    1.75    --   47.00-136.00  99.00   68
  8  ω   -145.00-118.00   0.50    7.00    -- -100.00-133.00 -81.00   54
  9  ω   -163.00 -93.00   0.50    7.00    -- -100.00  -6.00 -38.00  140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0042203000
_diffrn_orient_matrix_UB_12      -0.1523268000
_diffrn_orient_matrix_UB_13      -0.0278766000
_diffrn_orient_matrix_UB_21      0.0054302000
_diffrn_orient_matrix_UB_22      -0.1366224000
_diffrn_orient_matrix_UB_23      0.0308233000
_diffrn_orient_matrix_UB_31      -0.0893799000
_diffrn_orient_matrix_UB_32      -0.0152546000
_diffrn_orient_matrix_UB_33      0.0004729000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3629
_reflns_number_total             4783
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4783
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0573
_refine_ls_restrained_S_all      1.049
_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)+(0.0880P)²+1.9456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1464
_refine_ls_wR_factor_ref         0.1606
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C32(H32A,H32B), C33(H33A,H33B), C35(H35A,H35B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C12(H12), C15(H15), C17(H17), C22(H22), C23(H23), C25(H25),
 C26(H26), C27(H27), C29(H29), C30(H30), C31(H31), C34(H34)
2.c Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.52878(8) 0.9109(2) 0.43432(4) 0.0307(4) Uani 1 1 d . . . . .
O1 O 0.26885(8) 0.8220(2) 0.44869(5) 0.0346(4) Uani 1 1 d . . . . .
N1 N 0.39918(9) 0.8586(2) 0.44052(5) 0.0247(4) Uani 1 1 d . . . . .
C1 C 0.42651(11) 0.7172(3) 0.51038(6) 0.0223(4) Uani 1 1 d . . . . .
C2 C 0.56417(11) 0.7673(3) 0.50242(6) 0.0250(5) Uani 1 1 d . . . . .
H2 H 0.605318 0.809083 0.488496 0.030 Uiso 1 1 calc R . . . .
C3 C 0.48956(11) 0.7799(3) 0.48952(6) 0.0227(4) Uani 1 1 d . . . . .
C4 C 0.42273(11) 0.5864(3) 0.63032(6) 0.0236(4) Uani 1 1 d . . . . .
C5 C 0.44010(11) 0.6414(3) 0.54493(6) 0.0236(4) Uani 1 1 d . . . . .
C6 C 0.44359(10) 0.5700(3) 0.69566(6) 0.0252(4) Uani 1 1 d . . . . .
C7 C 0.34999(11) 0.7260(3) 0.49624(6) 0.0243(4) Uani 1 1 d . . . . .
C8 C 0.51827(11) 0.6301(3) 0.55697(6) 0.0250(4) Uani 1 1 d . . . . .
H8 H 0.528662 0.579433 0.579346 0.030 Uiso 1 1 calc R . . . .
C9 C 0.38456(11) 0.3018(3) 0.70531(7) 0.0274(5) Uani 1 1 d . . . . .
C10 C 0.39423(11) 0.3242(3) 0.66774(6) 0.0254(5) Uani 1 1 d . . . . .
C11 C 0.37541(11) 0.5725(3) 0.56492(6) 0.0248(4) Uani 1 1 d . . . . .
C12 C 0.43952(11) 0.7739(3) 0.63388(6) 0.0261(5) Uani 1 1 d . . . . .
H12 H 0.441893 0.844284 0.613259 0.031 Uiso 1 1 calc R . . . .
C13 C 0.44851(11) 0.7519(3) 0.70042(6) 0.0250(4) Uani 1 1 d . . . . .
C14 C 0.47606(11) 0.8547(3) 0.45306(6) 0.0244(4) Uani 1 1 d . . . . .
C15 C 0.57911(11) 0.6922(3) 0.53638(6) 0.0271(5) Uani 1 1 d . . . . .
H15 H 0.629872 0.684351 0.544923 0.032 Uiso 1 1 calc R . . . .
C16 C 0.34631(11) 0.2449(3) 0.64259(7) 0.0263(5) Uani 1 1 d . . . . .
C17 C 0.34814(12) 0.3271(3) 0.60784(6) 0.0267(5) Uani 1 1 d . . . . .
H17 H 0.323956 0.269029 0.588728 0.032 Uiso 1 1 calc R . . . .
C18 C 0.38447(11) 0.4907(3) 0.60109(6) 0.0256(5) Uani 1 1 d . . . . .
C19 C 0.41501(11) 0.4534(3) 0.72264(6) 0.0264(5) Uani 1 1 d . . . . .
C20 C 0.43095(11) 0.4897(3) 0.66172(6) 0.0254(5) Uani 1 1 d . . . . .
C21 C 0.33483(12) 0.8043(3) 0.46066(6) 0.0271(5) Uani 1 1 d . . . . .
C22 C 0.45230(11) 0.8524(3) 0.66750(6) 0.0265(5) Uani 1 1 d . . . . .
H22 H 0.463600 0.973484 0.668620 0.032 Uiso 1 1 calc R . . . .
C23 C 0.30227(11) 0.5777(3) 0.54938(6) 0.0268(5) Uani 1 1 d . . . . .
H23 H 0.260405 0.529166 0.561881 0.032 Uiso 1 1 calc R . . . .
C24 C 0.38986(12) 0.5110(3) 0.75587(6) 0.0294(5) Uani 1 1 d . . . . .
C25 C 0.28937(11) 0.6533(3) 0.51560(6) 0.0269(5) Uani 1 1 d . . . . .
H25 H 0.239373 0.654669 0.506013 0.032 Uiso 1 1 calc R . . . .
C26 C 0.43328(12) 0.8109(3) 0.73665(6) 0.0282(5) Uani 1 1 d . . . . .
H26 H 0.442072 0.929718 0.742474 0.034 Uiso 1 1 calc R . . . .
C27 C 0.40582(12) 0.6962(3) 0.76333(6) 0.0303(5) Uani 1 1 d . . . . .
H27 H 0.397575 0.739998 0.786477 0.036 Uiso 1 1 calc R . . . .
C28 C 0.32633(12) 0.1983(3) 0.72008(7) 0.0300(5) Uani 1 1 d . . . . .
C29 C 0.28328(12) 0.0942(3) 0.69415(7) 0.0315(5) Uani 1 1 d . . . . .
H29 H 0.248081 0.009496 0.702441 0.038 Uiso 1 1 calc R . . . .
C30 C 0.29266(12) 0.1164(3) 0.65735(7) 0.0311(5) Uani 1 1 d . . . . .
H30 H 0.263513 0.046344 0.641682 0.037 Uiso 1 1 calc R . . . .
C31 C 0.30942(13) 0.2379(3) 0.75714(7) 0.0321(5) Uani 1 1 d . . . . .
H31 H 0.276924 0.161957 0.770012 0.039 Uiso 1 1 calc R . . . .
C32 C 0.38572(12) 0.9265(3) 0.40387(6) 0.0290(5) Uani 1 1 d . . . . .
H32A H 0.422125 1.022273 0.398958 0.035 Uiso 1 1 calc R . . . .
H32B H 0.333522 0.975132 0.402370 0.035 Uiso 1 1 calc R . . . .
C33 C 0.39535(13) 0.7813(3) 0.37536(6) 0.0327(5) Uani 1 1 d . . . . .
H33A H 0.390176 0.835014 0.351685 0.039 Uiso 1 1 calc R . . . .
H33B H 0.447575 0.733064 0.377147 0.039 Uiso 1 1 calc R . . . .
C34 C 0.34015(13) 0.3864(3) 0.77433(7) 0.0328(5) Uani 1 1 d . . . . .
H34 H 0.328282 0.405974 0.798485 0.039 Uiso 1 1 calc R . . . .
C35 C 0.33729(13) 0.6281(3) 0.37836(7) 0.0329(5) Uani 1 1 d . . . . .
H35A H 0.342860 0.572842 0.401864 0.039 Uiso 1 1 calc R . . . .
H35B H 0.284969 0.675952 0.376779 0.039 Uiso 1 1 calc R . . . .
C36 C 0.34741(16) 0.4868(4) 0.34953(8) 0.0452(7) Uani 1 1 d . . . . .
H36A H 0.338533 0.538588 0.326210 0.068 Uiso 1 1 calc GR . . . .
H36B H 0.310767 0.392293 0.353506 0.068 Uiso 1 1 calc GR . . . .
H36C H 0.399343 0.440019 0.350603 0.068 Uiso 1 1 calc GR . . . .


_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
O2 C14 1.217(3) . ?
O1 C21 1.225(3) . ?
N1 C14 1.401(3) . ?
N1 C21 1.395(3) . ?
N1 C32 1.470(3) . ?
C1 C3 1.412(3) . ?
C1 C5 1.421(3) . ?
C1 C7 1.417(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.372(3) . ?
C2 C15 1.403(3) . ?
C3 C14 1.482(3) . ?
C4 C12 1.443(3) . ?
C4 C18 1.457(3) . ?
C4 C20 1.379(3) . ?
C5 C8 1.418(3) . ?
C5 C11 1.433(3) . ?
C6 C13 1.379(3) . ?
C6 C19 1.417(3) . ?
C6 C20 1.412(3) . ?
C7 C21 1.467(3) . ?
C7 C25 1.378(3) . ?
C8 H8 0.9300 . ?
C8 C15 1.376(3) . ?
C9 C10 1.413(3) . ?
C9 C19 1.408(3) . ?
C9 C28 1.381(3) . ?
C10 C16 1.379(3) . ?
C10 C20 1.411(3) . ?
C11 C18 1.483(3) . ?
C11 C23 1.383(3) . ?
C12 H12 0.9300 . ?
C12 C22 1.396(3) . ?
C13 C22 1.436(3) . ?
C13 C26 1.438(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.429(3) . ?
C16 C30 1.442(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.400(3) . ?
C19 C24 1.375(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C23 C25 1.393(3) . ?
C24 C27 1.444(3) . ?
C24 C34 1.440(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C26 C27 1.394(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.443(3) . ?
C28 C31 1.436(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.384(4) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C31 C34 1.388(4) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 C33 1.528(3) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C35 1.526(3) . ?
C34 H34 0.9300 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.516(4) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?

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
C14 N1 C32 117.56(17) . . ?
C21 N1 C14 124.31(19) . . ?
C21 N1 C32 118.13(17) . . ?
C3 C1 C5 120.06(18) . . ?
C3 C1 C7 119.6(2) . . ?
C7 C1 C5 120.30(19) . . ?
C3 C2 H2 119.6 . . ?
C3 C2 C15 120.76(19) . . ?
C15 C2 H2 119.6 . . ?
C1 C3 C14 120.37(17) . . ?
C2 C3 C1 120.2(2) . . ?
C2 C3 C14 119.37(19) . . ?
C12 C4 C18 129.7(2) . . ?
C20 C4 C12 114.6(2) . . ?
C20 C4 C18 114.48(19) . . ?
C1 C5 C11 118.90(18) . . ?
C8 C5 C1 117.61(19) . . ?
C8 C5 C11 123.4(2) . . ?
C13 C6 C19 122.8(2) . . ?
C13 C6 C20 123.1(2) . . ?
C20 C6 C19 108.18(19) . . ?
C1 C7 C21 121.04(19) . . ?
C25 C7 C1 119.4(2) . . ?
C25 C7 C21 119.51(18) . . ?
C5 C8 H8 119.2 . . ?
C15 C8 C5 121.7(2) . . ?
C15 C8 H8 119.2 . . ?
C19 C9 C10 108.07(19) . . ?
C28 C9 C10 122.9(2) . . ?
C28 C9 C19 122.9(2) . . ?
C16 C10 C9 123.0(2) . . ?
C16 C10 C20 122.7(2) . . ?
C20 C10 C9 108.3(2) . . ?
C5 C11 C18 122.39(18) . . ?
C23 C11 C5 118.7(2) . . ?
C23 C11 C18 118.92(19) . . ?
C4 C12 H12 119.2 . . ?
C22 C12 C4 121.7(2) . . ?
C22 C12 H12 119.2 . . ?
C6 C13 C22 114.5(2) . . ?
C6 C13 C26 114.4(2) . . ?
C22 C13 C26 129.8(2) . . ?
O2 C14 N1 120.3(2) . . ?
O2 C14 C3 122.37(18) . . ?
N1 C14 C3 117.28(17) . . ?
C2 C15 H15 120.2 . . ?
C8 C15 C2 119.65(18) . . ?
C8 C15 H15 120.2 . . ?
C10 C16 C17 114.22(19) . . ?
C10 C16 C30 114.4(2) . . ?
C17 C16 C30 130.2(2) . . ?
C16 C17 H17 118.3 . . ?
C18 C17 C16 123.3(2) . . ?
C18 C17 H17 118.3 . . ?
C4 C18 C11 121.05(19) . . ?
C17 C18 C4 120.1(2) . . ?
C17 C18 C11 118.5(2) . . ?
C9 C19 C6 107.8(2) . . ?
C24 C19 C6 123.2(2) . . ?
C24 C19 C9 123.1(2) . . ?
C4 C20 C6 122.9(2) . . ?
C4 C20 C10 123.4(2) . . ?
C10 C20 C6 107.69(19) . . ?
O1 C21 N1 120.5(2) . . ?
O1 C21 C7 122.25(19) . . ?
N1 C21 C7 117.23(18) . . ?
C12 C22 C13 122.0(2) . . ?
C12 C22 H22 119.0 . . ?
C13 C22 H22 119.0 . . ?
C11 C23 H23 119.0 . . ?
C11 C23 C25 122.04(19) . . ?
C25 C23 H23 119.0 . . ?
C19 C24 C27 114.5(2) . . ?
C19 C24 C34 114.1(2) . . ?
C34 C24 C27 130.3(2) . . ?
C7 C25 C23 120.63(19) . . ?
C7 C25 H25 119.7 . . ?
C23 C25 H25 119.7 . . ?
C13 C26 H26 118.9 . . ?
C27 C26 C13 122.3(2) . . ?
C27 C26 H26 118.9 . . ?
C24 C27 H27 119.2 . . ?
C26 C27 C24 121.6(2) . . ?
C26 C27 H27 119.2 . . ?
C9 C28 C29 114.3(2) . . ?
C9 C28 C31 114.2(2) . . ?
C31 C28 C29 130.3(2) . . ?
C28 C29 H29 118.9 . . ?
C30 C29 C28 122.2(2) . . ?
C30 C29 H29 118.9 . . ?
C16 C30 H30 119.0 . . ?
C29 C30 C16 121.9(2) . . ?
C29 C30 H30 119.0 . . ?
C28 C31 H31 119.0 . . ?
C34 C31 C28 121.9(2) . . ?
C34 C31 H31 119.0 . . ?
N1 C32 H32A 109.2 . . ?
N1 C32 H32B 109.2 . . ?
N1 C32 C33 112.02(19) . . ?
H32A C32 H32B 107.9 . . ?
C33 C32 H32A 109.2 . . ?
C33 C32 H32B 109.2 . . ?
C32 C33 H33A 108.6 . . ?
C32 C33 H33B 108.6 . . ?
H33A C33 H33B 107.6 . . ?
C35 C33 C32 114.60(19) . . ?
C35 C33 H33A 108.6 . . ?
C35 C33 H33B 108.6 . . ?
C24 C34 H34 119.0 . . ?
C31 C34 C24 121.9(2) . . ?
C31 C34 H34 119.0 . . ?
C33 C35 H35A 108.8 . . ?
C33 C35 H35B 108.8 . . ?
H35A C35 H35B 107.7 . . ?
C36 C35 C33 113.6(2) . . ?
C36 C35 H35A 108.8 . . ?
C36 C35 H35B 108.8 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

_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 4.041
_oxdiff_exptl_absorpt_empirical_full_min 0.567
####################################################################### 
# 
# 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_045103_wyl_100k_a
_database_code_depnum_ccdc_archive 'CCDC 2075924'
loop_
_audit_author_name
_audit_author_address
'Jun Xu'
;Tianjin University
China
;
_audit_update_record             
;
2021-04-07 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_audit_creation_date             2021-03-31
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H25 B F2 N2'
_chemical_formula_sum            'C34 H25 B F2 N2'
_chemical_formula_weight         510.37
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.15670(10)
_cell_length_b                   7.75280(10)
_cell_length_c                   34.6394(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.1160(10)
_cell_angle_gamma                90
_cell_volume                     2458.59(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16262
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.5230
_cell_measurement_theta_min      2.5480
_shelx_estimated_absorpt_T_max   0.931
_shelx_estimated_absorpt_T_min   0.899
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            24826
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.805
_diffrn_reflns_theta_min         2.552
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -47.00   0.50    0.07    --  -45.62 -82.00   3.00  122
  2  ω    -64.00  15.00   0.50    0.07    --  -45.62  82.00 125.00  158
  3  ω     -8.00  69.00   0.50    0.07    --   45.62 -82.00   3.00  154
  4  ω   -148.00-123.00   0.50    0.29    -- -100.00 -82.00   3.00   50
  5  ω    -75.00 -29.00   0.50    0.29    -- -100.00  82.00 125.00   92
  6  ω     76.00 152.00   0.50    0.29    --  101.75  82.00 125.00  152
  7  ω     29.00 127.00   0.50    0.29    --  101.75 -82.00   3.00  196
  8  ω   -111.00 -85.00   0.50    0.07    --  -45.62-125.00-180.00   52
  9  ω   -118.00 -77.00   0.50    0.07    --  -45.62-125.00 150.00   82
 10  ω    -56.00  24.00   0.50    0.07    --  -45.62  38.00 120.00  160
 11  ω   -172.00 -84.00   0.50    0.29    -- -100.00 -30.00-150.00  176
 12  ω   -174.00 -88.00   0.50    0.29    -- -100.00 -30.00  30.00  172
 13  ω   -174.00 -82.00   0.50    0.29    -- -100.00 -15.00-120.00  184
 14  ω   -109.00 -29.00   0.50    0.29    -- -100.00  61.00 -30.00  160
 15  ω   -152.00 -98.00   0.50    0.29    -- -100.00 -61.00 -30.00  108
 16  ω     96.00 121.00   0.50    0.29    --  101.75  45.00-150.00   50
 17  ω    136.00 169.00   0.50    0.29    --  101.75  45.00 -90.00   66
 18  ω     60.00  98.00   0.50    0.29    --  101.75 -45.00 120.00   76
 19  ω     30.00  85.00   0.50    0.29    --  101.75 -45.00  30.00  110
 20  ω     88.00 168.00   0.50    0.29    --  101.75  45.00  90.00  160
 21  ω     27.00 117.00   0.50    0.29    --  101.75 -15.00 -30.00  180
 22  ω     89.00 167.00   0.50    0.29    --  101.75  45.00  60.00  156
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0339749000
_diffrn_orient_matrix_UB_12      -0.0743387000
_diffrn_orient_matrix_UB_13      0.0404312000
_diffrn_orient_matrix_UB_21      0.0762557000
_diffrn_orient_matrix_UB_22      -0.1556728000
_diffrn_orient_matrix_UB_23      -0.0184949000
_diffrn_orient_matrix_UB_31      0.1461526000
_diffrn_orient_matrix_UB_32      0.0985643000
_diffrn_orient_matrix_UB_33      0.0012553000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4500
_reflns_number_total             4897
_reflns_odcompleteness_completeness 99.98
_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 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         4897
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.039
_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)+(0.0523P)²+1.1375P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1096
_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), C16(H16), C19(H19), C21(H21), C22(H22), C24(H24), C26(H26), C27(H27),
 C28(H28), C32(H32)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C33(H33A,H33B,
 H33C), C34(H34A,H34B,H34C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.86051(10) 0.86141(11) 0.53722(2) 0.0355(2) Uani 1 1 d . . . . .
F2 F 0.86458(10) 0.57424(12) 0.52522(2) 0.0380(2) Uani 1 1 d . . . . .
N1 N 0.65651(13) 0.68946(15) 0.55759(3) 0.0268(3) Uani 1 1 d . . . . .
N2 N 0.69364(14) 0.74967(16) 0.48849(3) 0.0304(3) Uani 1 1 d . . . . .
C1 C 0.49309(15) 0.49910(18) 0.73215(4) 0.0266(3) Uani 1 1 d . . . . .
C2 C 0.49814(15) 0.51558(18) 0.77284(4) 0.0276(3) Uani 1 1 d . . . . .
C3 C 0.59074(15) 0.40246(17) 0.71192(4) 0.0261(3) Uani 1 1 d . . . . .
C4 C 0.39369(14) 0.76019(19) 0.74777(4) 0.0278(3) Uani 1 1 d . . . . .
C5 C 0.42744(14) 0.65025(18) 0.71668(4) 0.0268(3) Uani 1 1 d . . . . .
C6 C 0.68300(16) 0.64640(17) 0.59476(4) 0.0270(3) Uani 1 1 d . . . . .
C7 C 0.69232(16) 0.31146(18) 0.77555(4) 0.0290(3) Uani 1 1 d . . . . .
H7 H 0.755953 0.241147 0.789671 0.035 Uiso 1 1 calc R . . . .
C8 C 0.50592(16) 0.70943(18) 0.55174(4) 0.0271(3) Uani 1 1 d . . . . .
C9 C 0.53186(15) 0.59131(18) 0.65534(4) 0.0279(3) Uani 1 1 d . . . . .
C10 C 0.54188(17) 0.76965(18) 0.48352(4) 0.0293(3) Uani 1 1 d . . . . .
C11 C 0.45242(15) 0.70974(18) 0.67990(4) 0.0277(3) Uani 1 1 d . . . . .
C12 C 0.55006(16) 0.63531(18) 0.61415(4) 0.0281(3) Uani 1 1 d . . . . .
C13 C 0.43586(15) 0.67619(19) 0.78246(4) 0.0283(3) Uani 1 1 d . . . . .
C14 C 0.43751(16) 0.67530(18) 0.58731(4) 0.0290(3) Uani 1 1 d . . . . .
C15 C 0.38595(15) 0.93684(19) 0.74425(4) 0.0297(3) Uani 1 1 d . . . . .
C16 C 0.59902(15) 0.44513(18) 0.67145(4) 0.0277(3) Uani 1 1 d . . . . .
H16 H 0.651162 0.372455 0.655395 0.033 Uiso 1 1 calc R . . . .
C17 C 0.60259(16) 0.43360(19) 0.79576(4) 0.0292(3) Uani 1 1 d . . . . .
C18 C 0.47113(16) 0.7640(2) 0.81604(4) 0.0310(3) Uani 1 1 d . . . . .
C19 C 0.68629(16) 0.29608(18) 0.73575(4) 0.0289(3) Uani 1 1 d . . . . .
H19 H 0.745412 0.214951 0.723929 0.035 Uiso 1 1 calc R . . . .
C20 C 0.44893(17) 0.75441(17) 0.51492(4) 0.0293(3) Uani 1 1 d . . . . .
C21 C 0.39175(16) 0.99924(19) 0.70508(5) 0.0323(3) Uani 1 1 d . . . . .
H21 H 0.374118 1.115445 0.700230 0.039 Uiso 1 1 calc R . . . .
C22 C 0.42277(15) 0.89126(19) 0.67452(4) 0.0304(3) Uani 1 1 d . . . . .
H22 H 0.424595 0.936991 0.649714 0.037 Uiso 1 1 calc R . . . .
C23 C 0.83380(16) 0.6200(2) 0.61055(4) 0.0304(3) Uani 1 1 d . . . . .
H23A H 0.870846 0.511503 0.601640 0.046 Uiso 1 1 calc GR . . . .
H23B H 0.832012 0.619856 0.638247 0.046 Uiso 1 1 calc GR . . . .
H23C H 0.895755 0.711558 0.601926 0.046 Uiso 1 1 calc GR . . . .
C24 C 0.43894(16) 0.9462(2) 0.81434(4) 0.0341(3) Uani 1 1 d . . . . .
H24 H 0.444630 1.010345 0.837005 0.041 Uiso 1 1 calc R . . . .
C25 C 0.51447(19) 0.80337(19) 0.44339(4) 0.0348(3) Uani 1 1 d . . . . .
C26 C 0.62438(17) 0.5110(2) 0.83330(4) 0.0330(3) Uani 1 1 d . . . . .
H26 H 0.682775 0.454425 0.851556 0.040 Uiso 1 1 calc R . . . .
C27 C 0.56102(17) 0.6669(2) 0.84299(4) 0.0333(3) Uani 1 1 d . . . . .
H27 H 0.576906 0.710595 0.867724 0.040 Uiso 1 1 calc R . . . .
C28 C 0.40007(16) 1.0287(2) 0.78039(5) 0.0331(3) Uani 1 1 d . . . . .
H28 H 0.382457 1.146777 0.780790 0.040 Uiso 1 1 calc R . . . .
C29 C 0.75762(19) 0.7717(2) 0.45412(4) 0.0355(3) Uani 1 1 d . . . . .
C30 C 0.27803(17) 0.6689(2) 0.59590(5) 0.0366(3) Uani 1 1 d . . . . .
H30A H 0.239657 0.784103 0.596599 0.055 Uiso 1 1 calc GR . . . .
H30B H 0.264564 0.614474 0.620465 0.055 Uiso 1 1 calc GR . . . .
H30C H 0.227579 0.604146 0.576146 0.055 Uiso 1 1 calc GR . . . .
C31 C 0.28917(18) 0.7893(2) 0.51000(5) 0.0363(3) Uani 1 1 d . . . . .
H31A H 0.238073 0.682337 0.506118 0.054 Uiso 1 1 calc GR . . . .
H31B H 0.272997 0.862635 0.488006 0.054 Uiso 1 1 calc GR . . . .
H31C H 0.253801 0.845169 0.532708 0.054 Uiso 1 1 calc GR . . . .
C32 C 0.6484(2) 0.8028(2) 0.42602(4) 0.0387(4) Uani 1 1 d . . . . .
H32 H 0.663984 0.820243 0.399854 0.046 Uiso 1 1 calc R . . . .
C33 C 0.3715(2) 0.8307(2) 0.42231(5) 0.0419(4) Uani 1 1 d . . . . .
H33A H 0.306860 0.736587 0.427695 0.063 Uiso 1 1 calc GR . . . .
H33B H 0.387838 0.836197 0.395049 0.063 Uiso 1 1 calc GR . . . .
H33C H 0.328358 0.936772 0.430720 0.063 Uiso 1 1 calc GR . . . .
C34 C 0.9187(2) 0.7668(3) 0.44923(5) 0.0453(4) Uani 1 1 d . . . . .
H34A H 0.963387 0.857833 0.464082 0.068 Uiso 1 1 calc GR . . . .
H34B H 0.940655 0.781902 0.422452 0.068 Uiso 1 1 calc GR . . . .
H34C H 0.955988 0.657627 0.458001 0.068 Uiso 1 1 calc GR . . . .
B1 B 0.77456(18) 0.7186(2) 0.52730(4) 0.0285(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
F1 B1 1.3977(19) . ?
F2 B1 1.3924(18) . ?
N1 C6 1.3474(18) . ?
N1 C8 1.3984(18) . ?
N1 B1 1.538(2) . ?
N2 C10 1.405(2) . ?
N2 C29 1.3482(19) . ?
N2 B1 1.5412(19) . ?
C1 C2 1.4153(19) . ?
C1 C3 1.370(2) . ?
C1 C5 1.417(2) . ?
C2 C13 1.412(2) . ?
C2 C17 1.385(2) . ?
C3 C16 1.4440(19) . ?
C3 C19 1.449(2) . ?
C4 C5 1.412(2) . ?
C4 C13 1.414(2) . ?
C4 C15 1.377(2) . ?
C5 C11 1.378(2) . ?
C6 C12 1.404(2) . ?
C6 C23 1.489(2) . ?
C7 H7 0.9300 . ?
C7 C17 1.444(2) . ?
C7 C19 1.384(2) . ?
C8 C14 1.418(2) . ?
C8 C20 1.4121(19) . ?
C9 C11 1.456(2) . ?
C9 C12 1.4798(19) . ?
C9 C16 1.400(2) . ?
C10 C20 1.399(2) . ?
C10 C25 1.432(2) . ?
C11 C22 1.445(2) . ?
C12 C14 1.409(2) . ?
C13 C18 1.381(2) . ?
C14 C30 1.497(2) . ?
C15 C21 1.442(2) . ?
C15 C28 1.444(2) . ?
C16 H16 0.9300 . ?
C17 C26 1.442(2) . ?
C18 C24 1.444(2) . ?
C18 C27 1.444(2) . ?
C19 H19 0.9300 . ?
C20 C31 1.494(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.383(2) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24 0.9300 . ?
C24 C28 1.379(2) . ?
C25 C32 1.377(3) . ?
C25 C33 1.502(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.385(2) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 C32 1.403(2) . ?
C29 C34 1.488(3) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32 0.9300 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?

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 C8 108.95(12) . . ?
C6 N1 B1 124.92(12) . . ?
C8 N1 B1 126.09(12) . . ?
C10 N2 B1 125.56(12) . . ?
C29 N2 C10 108.87(12) . . ?
C29 N2 B1 125.48(13) . . ?
C2 C1 C5 107.89(12) . . ?
C3 C1 C2 123.36(13) . . ?
C3 C1 C5 122.35(13) . . ?
C13 C2 C1 107.99(12) . . ?
C17 C2 C1 122.56(13) . . ?
C17 C2 C13 123.15(13) . . ?
C1 C3 C16 114.74(13) . . ?
C1 C3 C19 114.39(13) . . ?
C16 C3 C19 129.87(13) . . ?
C5 C4 C13 108.05(13) . . ?
C15 C4 C5 122.99(14) . . ?
C15 C4 C13 123.11(14) . . ?
C4 C5 C1 107.96(12) . . ?
C11 C5 C1 123.32(13) . . ?
C11 C5 C4 123.06(13) . . ?
N1 C6 C12 109.30(12) . . ?
N1 C6 C23 122.22(13) . . ?
C12 C6 C23 128.47(13) . . ?
C17 C7 H7 119.1 . . ?
C19 C7 H7 119.1 . . ?
C19 C7 C17 121.85(13) . . ?
N1 C8 C14 107.71(12) . . ?
N1 C8 C20 120.29(13) . . ?
C20 C8 C14 132.00(14) . . ?
C11 C9 C12 119.01(12) . . ?
C16 C9 C11 119.88(13) . . ?
C16 C9 C12 120.93(12) . . ?
N2 C10 C25 107.06(13) . . ?
C20 C10 N2 120.69(12) . . ?
C20 C10 C25 132.26(14) . . ?
C5 C11 C9 115.02(13) . . ?
C5 C11 C22 114.28(13) . . ?
C22 C11 C9 129.32(13) . . ?
C6 C12 C9 126.17(13) . . ?
C6 C12 C14 107.50(12) . . ?
C14 C12 C9 126.32(13) . . ?
C2 C13 C4 108.10(12) . . ?
C18 C13 C2 122.99(14) . . ?
C18 C13 C4 122.99(14) . . ?
C8 C14 C30 128.91(13) . . ?
C12 C14 C8 106.53(13) . . ?
C12 C14 C30 124.44(13) . . ?
C4 C15 C21 114.47(13) . . ?
C4 C15 C28 114.21(14) . . ?
C21 C15 C28 130.24(14) . . ?
C3 C16 H16 118.6 . . ?
C9 C16 C3 122.77(13) . . ?
C9 C16 H16 118.6 . . ?
C2 C17 C7 114.58(13) . . ?
C2 C17 C26 114.06(13) . . ?
C26 C17 C7 129.79(14) . . ?
C13 C18 C24 113.82(14) . . ?
C13 C18 C27 114.13(14) . . ?
C24 C18 C27 130.50(14) . . ?
C3 C19 H19 119.0 . . ?
C7 C19 C3 122.03(13) . . ?
C7 C19 H19 119.0 . . ?
C8 C20 C31 119.44(13) . . ?
C10 C20 C8 120.22(13) . . ?
C10 C20 C31 120.33(13) . . ?
C15 C21 H21 119.0 . . ?
C22 C21 C15 121.92(14) . . ?
C22 C21 H21 119.0 . . ?
C11 C22 H22 118.9 . . ?
C21 C22 C11 122.11(14) . . ?
C21 C22 H22 118.9 . . ?
C6 C23 H23A 109.5 . . ?
C6 C23 H23B 109.5 . . ?
C6 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C18 C24 H24 118.7 . . ?
C28 C24 C18 122.50(14) . . ?
C28 C24 H24 118.7 . . ?
C10 C25 C33 129.23(16) . . ?
C32 C25 C10 106.44(14) . . ?
C32 C25 C33 124.32(14) . . ?
C17 C26 H26 119.0 . . ?
C27 C26 C17 122.03(14) . . ?
C27 C26 H26 119.0 . . ?
C18 C27 H27 118.9 . . ?
C26 C27 C18 122.29(13) . . ?
C26 C27 H27 118.9 . . ?
C15 C28 H28 119.1 . . ?
C24 C28 C15 121.87(14) . . ?
C24 C28 H28 119.1 . . ?
N2 C29 C32 108.57(15) . . ?
N2 C29 C34 123.09(14) . . ?
C32 C29 C34 128.32(14) . . ?
C14 C30 H30A 109.5 . . ?
C14 C30 H30B 109.5 . . ?
C14 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C20 C31 H31A 109.5 . . ?
C20 C31 H31B 109.5 . . ?
C20 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C25 C32 C29 109.05(14) . . ?
C25 C32 H32 125.5 . . ?
C29 C32 H32 125.5 . . ?
C25 C33 H33A 109.5 . . ?
C25 C33 H33B 109.5 . . ?
C25 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C29 C34 H34A 109.5 . . ?
C29 C34 H34B 109.5 . . ?
C29 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
F1 B1 N1 110.39(11) . . ?
F1 B1 N2 110.44(12) . . ?
F2 B1 F1 108.57(12) . . ?
F2 B1 N1 110.01(12) . . ?
F2 B1 N2 110.83(12) . . ?
N1 B1 N2 106.60(12) . . ?

_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 1.253
_oxdiff_exptl_absorpt_empirical_full_min 0.900
