# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_ia423c
_database_code_depnum_ccdc_archive 'CCDC 2257907'
loop_
_audit_author_name
_audit_author_address
'Qingkai Qi'
;Dartmouth College
United States of America
;
_audit_update_record             
;
2023-04-20 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;
_audit_creation_date             2023-04-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 B F2 N4 O'
_chemical_formula_sum            'C19 H15 B F2 N4 O'
_chemical_formula_weight         364.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H15BF2N4O
_chemical_oxdiff_usercomment     AzoBF2-2C
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'
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                   17.0351(2)
_cell_length_b                   7.02387(10)
_cell_length_c                   27.7571(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3321.20(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6612
_cell_measurement_temperature    100.09(10)
_cell_measurement_theta_max      79.0250
_cell_measurement_theta_min      3.1800
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.839
_exptl_absorpt_coefficient_mu    0.904
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark yellow'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1504
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0958
0 1 0 0.1065
0 0 -1 0.0085
0 0 1 0.0085
-1 0 0 0.0204
1 0 0 0.0162
1 0 1 0.0148
-1 0 -1 0.0176

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.017
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0003 -0.9995 0.0033 0.0264 -0.2116 0.0510
-0.0003 0.9995 -0.0033 -0.0264 0.2116 -0.0510
-0.0003 -0.0001 -0.9986 -0.0505 -0.0008 0.0229
0.0003 0.0001 0.9986 0.0505 0.0008 -0.0229
-0.9996 -0.0004 -0.0007 0.0356 0.0236 0.0797
0.9996 0.0004 0.0007 -0.0356 -0.0236 -0.0797
0.9998 0.0005 0.9993 0.0148 -0.0228 -0.1025
-0.9998 -0.0005 -0.9993 -0.0148 0.0228 0.1025

_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus.  A suitable 
crystal was chosen and mounted on a nylon loop using Paratone oil.  Data  were 
measured based on the Pre-Experiment plugin of CrysAlisPro software.  Cell 
parameters were retrieved using CrysAlisPro software and data reduction was 
performed using the intergration software inside the CrysAlisPro which 
corrects for Lp.  The structure was solved by the direct method using the 
SHELXT program and refined by least squares method on F2, SHELXL,
 incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            18821
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.464
_diffrn_reflns_theta_min         3.184
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.09(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -76.00  26.00   0.50    2.50    --  -47.10  90.00  58.00  204
  2  ω    -47.00 -18.00   0.50   10.00    --  -91.75  37.00 -68.00   58
  3  ω    -79.00 -22.00   0.50   10.00    --  -91.75 108.00 145.00  114
  4  ω    101.00 178.00   0.50   10.00    --  113.25  37.00 -68.00  154
  5  ω     42.00 104.00   0.50   10.00    --  113.25 -90.00 -56.00  124
  6  ω   -120.00 -35.00   0.50    2.50    --  -47.10 -37.00-150.00  170
  7  ω    -39.00  28.00   0.50    2.50    --  -47.10  19.00 150.00  134
  8  ω     42.00  69.00   0.50   10.00    --  113.25 -61.00 -60.00   54
  9  ω     42.00  69.00   0.50   10.00    --  113.25 -61.00 -30.00   54
 10  ω     42.00 104.00   0.50   10.00    --  113.25 -94.00-150.00  124
 11  ω     42.00  67.00   0.50   10.00    --  113.25 -61.00 150.00   50
 12  ω     77.00 103.00   0.50   10.00    --  113.25 -94.00   0.00   52
 13  ω     45.00  71.00   0.50   10.00    --  113.25 -94.00   0.00   52
 14  ω    103.00 135.00   0.50   10.00    --  113.25  45.00-150.00   64
 15  ω    148.00 174.00   0.50   10.00    --  113.25  45.00-150.00   52
 16  ω     42.00  67.00   0.50   10.00    --  113.25 -61.00-120.00   50
 17  ω     42.00  67.00   0.50   10.00    --  113.25 -61.00  30.00   50
 18  ω     42.00  67.00   0.50   10.00    --  113.25 -61.00 120.00   50
 19  ω     42.00  67.00   0.50   10.00    --  113.25 -61.00-150.00   50
 20  ω    109.00 169.00   0.50   10.00    --  113.25 108.00 145.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0356743000
_diffrn_orient_matrix_UB_12      -0.0262175000
_diffrn_orient_matrix_UB_13      0.0505653000
_diffrn_orient_matrix_UB_21      -0.0236660000
_diffrn_orient_matrix_UB_22      0.2116710000
_diffrn_orient_matrix_UB_23      0.0007470000
_diffrn_orient_matrix_UB_31      -0.0796596000
_diffrn_orient_matrix_UB_32      -0.0511083000
_diffrn_orient_matrix_UB_33      -0.0228734000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3100
_reflns_number_total             3575
_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 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3575
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.073
_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)+(0.0371P)²+1.3853P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0930
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_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:
 C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C16(H16),
 C17(H17)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_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 0.42569(5) 0.57105(12) 0.47106(3) 0.02384(19) Uani 1 1 d . . . . .
F2 F 0.43341(5) 0.89510(12) 0.46482(3) 0.02410(19) Uani 1 1 d . . . . .
O1 O 0.61175(5) 0.77783(13) 0.27547(3) 0.0194(2) Uani 1 1 d . . . . .
N1 N 0.32386(6) 0.74111(15) 0.42245(4) 0.0163(2) Uani 1 1 d . . . . .
N2 N 0.33116(6) 0.77104(16) 0.37689(4) 0.0178(2) Uani 1 1 d . . . . .
N3 N 0.32359(6) 0.75175(16) 0.50927(4) 0.0168(2) Uani 1 1 d . . . . .
N4 N 0.12593(7) 0.74548(18) 0.38790(4) 0.0245(3) Uani 1 1 d . . . . .
C1 C 0.24912(8) 0.73254(18) 0.44102(4) 0.0178(3) Uani 1 1 d . . . . .
C2 C 0.24963(8) 0.73717(18) 0.49182(4) 0.0174(2) Uani 1 1 d . . . . .
C3 C 0.18412(8) 0.72799(19) 0.52303(5) 0.0196(3) Uani 1 1 d . . . . .
H3 H 0.132384 0.718418 0.510493 0.024 Uiso 1 1 calc R U . . .
C4 C 0.19679(8) 0.73315(19) 0.57130(5) 0.0202(3) Uani 1 1 d . . . . .
H4 H 0.153459 0.723462 0.592704 0.024 Uiso 1 1 calc R U . . .
C5 C 0.27423(8) 0.75290(17) 0.59045(5) 0.0183(3) Uani 1 1 d . . . . .
C6 C 0.28878(8) 0.76766(19) 0.64045(5) 0.0216(3) Uani 1 1 d . . . . .
H6 H 0.246479 0.759131 0.662647 0.026 Uiso 1 1 calc R U . . .
C7 C 0.36388(9) 0.7943(2) 0.65699(5) 0.0231(3) Uani 1 1 d . . . . .
H7 H 0.373288 0.805883 0.690597 0.028 Uiso 1 1 calc R U . . .
C8 C 0.42697(8) 0.8045(2) 0.62446(5) 0.0227(3) Uani 1 1 d . . . . .
H8 H 0.478608 0.824082 0.636387 0.027 Uiso 1 1 calc R U . . .
C9 C 0.41515(8) 0.78644(19) 0.57551(5) 0.0198(3) Uani 1 1 d . . . . .
H9 H 0.458304 0.790629 0.553856 0.024 Uiso 1 1 calc R U . . .
C10 C 0.33817(8) 0.76173(18) 0.55812(5) 0.0174(3) Uani 1 1 d . . . . .
C11 C 0.18160(8) 0.73930(19) 0.41140(5) 0.0185(3) Uani 1 1 d . . . . .
C12 C 0.40534(7) 0.77031(18) 0.35512(5) 0.0169(3) Uani 1 1 d . . . . .
C13 C 0.47098(7) 0.66119(19) 0.36843(5) 0.0178(3) Uani 1 1 d . . . . .
H13 H 0.469210 0.583677 0.396455 0.021 Uiso 1 1 calc R U . . .
C14 C 0.53796(7) 0.66721(19) 0.34060(4) 0.0175(3) Uani 1 1 d . . . . .
H14 H 0.582084 0.592482 0.349561 0.021 Uiso 1 1 calc R U . . .
C15 C 0.54208(7) 0.78152(18) 0.29937(4) 0.0166(3) Uani 1 1 d . . . . .
C16 C 0.47652(7) 0.88642(19) 0.28508(5) 0.0182(3) Uani 1 1 d . . . . .
H16 H 0.478188 0.962336 0.256774 0.022 Uiso 1 1 calc R U . . .
C17 C 0.40898(8) 0.87818(19) 0.31280(5) 0.0185(3) Uani 1 1 d . . . . .
H17 H 0.363960 0.947567 0.302812 0.022 Uiso 1 1 calc R U . . .
C18 C 0.61814(8) 0.88919(19) 0.23210(5) 0.0194(3) Uani 1 1 d . . . . .
H18A H 0.598762 1.020178 0.237751 0.023 Uiso 1 1 calc R U . . .
H18B H 0.586611 0.831087 0.205990 0.023 Uiso 1 1 calc R U . . .
C19 C 0.70368(8) 0.8928(2) 0.21841(5) 0.0238(3) Uani 1 1 d . . . . .
H19A H 0.710597 0.970021 0.189322 0.036 Uiso 1 1 calc R U . . .
H19B H 0.721775 0.762617 0.212182 0.036 Uiso 1 1 calc R U . . .
H19C H 0.734328 0.947934 0.244827 0.036 Uiso 1 1 calc R U . . .
B1 B 0.38632(9) 0.7394(2) 0.46786(5) 0.0184(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 1.3621(17) . ?
F2 B1 1.3591(17) . ?
O1 C15 1.3600(15) . ?
O1 C18 1.4397(15) . ?
N1 N2 1.2879(15) . ?
N1 C1 1.3749(16) . ?
N1 B1 1.6495(17) . ?
N2 C12 1.4007(16) . ?
N3 C2 1.3536(17) . ?
N3 C10 1.3805(17) . ?
N3 B1 1.5719(18) . ?
N4 C11 1.1519(18) . ?
C1 C2 1.4105(17) . ?
C1 C11 1.4145(18) . ?
C2 C3 1.4142(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.3576(19) . ?
C4 H4 0.9500 . ?
C4 C5 1.4289(19) . ?
C5 C6 1.4138(18) . ?
C5 C10 1.4125(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.372(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.405(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.3794(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.4082(18) . ?
C12 C13 1.4051(18) . ?
C12 C17 1.3991(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.3785(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.3997(18) . ?
C15 C16 1.3955(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.3854(18) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5061(18) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O1 C18 117.62(10) . . ?
N2 N1 C1 117.69(11) . . ?
N2 N1 B1 133.57(10) . . ?
C1 N1 B1 108.09(10) . . ?
N1 N2 C12 120.67(11) . . ?
C2 N3 C10 121.52(11) . . ?
C2 N3 B1 111.53(10) . . ?
C10 N3 B1 126.79(11) . . ?
N1 C1 C2 111.59(11) . . ?
N1 C1 C11 122.25(11) . . ?
C2 C1 C11 125.82(12) . . ?
N3 C2 C1 111.42(11) . . ?
N3 C2 C3 121.25(11) . . ?
C1 C2 C3 127.33(12) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 C2 118.55(12) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.09(12) . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 122.29(12) . . ?
C10 C5 C4 118.68(12) . . ?
C10 C5 C6 119.02(12) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.13(13) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.33(13) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.11(13) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 120.5 . . ?
C8 C9 C10 119.00(12) . . ?
C10 C9 H9 120.5 . . ?
N3 C10 C5 118.88(12) . . ?
N3 C10 C9 120.70(12) . . ?
C9 C10 C5 120.39(12) . . ?
N4 C11 C1 178.93(14) . . ?
N2 C12 C13 127.33(12) . . ?
C17 C12 N2 113.59(11) . . ?
C17 C12 C13 118.74(12) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.64(12) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.15(12) . . ?
C15 C14 H14 119.4 . . ?
O1 C15 C14 115.58(11) . . ?
O1 C15 C16 124.73(11) . . ?
C16 C15 C14 119.68(11) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.00(12) . . ?
C17 C16 H16 120.5 . . ?
C12 C17 H17 119.1 . . ?
C16 C17 C12 121.71(12) . . ?
C16 C17 H17 119.1 . . ?
O1 C18 H18A 110.3 . . ?
O1 C18 H18B 110.3 . . ?
O1 C18 C19 107.04(10) . . ?
H18A C18 H18B 108.6 . . ?
C19 C18 H18A 110.3 . . ?
C19 C18 H18B 110.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
F1 B1 N1 111.96(11) . . ?
F1 B1 N3 109.58(11) . . ?
F2 B1 F1 114.33(11) . . ?
F2 B1 N1 109.10(10) . . ?
F2 B1 N3 113.70(11) . . ?
N3 B1 N1 96.88(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C15 C16 C17 -179.82(12) . . . . ?
N1 N2 C12 C13 32.03(19) . . . . ?
N1 N2 C12 C17 -154.73(12) . . . . ?
N1 C1 C2 N3 0.92(15) . . . . ?
N1 C1 C2 C3 -178.93(12) . . . . ?
N2 N1 C1 C2 -168.29(11) . . . . ?
N2 N1 C1 C11 5.43(18) . . . . ?
N2 N1 B1 F1 -81.48(17) . . . . ?
N2 N1 B1 F2 46.09(18) . . . . ?
N2 N1 B1 N3 164.15(13) . . . . ?
N2 C12 C13 C14 174.96(12) . . . . ?
N2 C12 C17 C16 -176.77(12) . . . . ?
N3 C2 C3 C4 -0.33(19) . . . . ?
C1 N1 N2 C12 -176.22(11) . . . . ?
C1 N1 B1 F1 108.33(12) . . . . ?
C1 N1 B1 F2 -124.09(11) . . . . ?
C1 N1 B1 N3 -6.03(13) . . . . ?
C1 C2 C3 C4 179.51(13) . . . . ?
C2 N3 C10 C5 1.18(18) . . . . ?
C2 N3 C10 C9 -176.80(12) . . . . ?
C2 N3 B1 F1 -109.53(12) . . . . ?
C2 N3 B1 F2 121.14(12) . . . . ?
C2 N3 B1 N1 6.75(13) . . . . ?
C2 C3 C4 C5 1.8(2) . . . . ?
C3 C4 C5 C6 176.96(13) . . . . ?
C3 C4 C5 C10 -1.75(19) . . . . ?
C4 C5 C6 C7 -177.32(13) . . . . ?
C4 C5 C10 N3 0.26(18) . . . . ?
C4 C5 C10 C9 178.24(12) . . . . ?
C5 C6 C7 C8 -0.9(2) . . . . ?
C6 C5 C10 N3 -178.50(12) . . . . ?
C6 C5 C10 C9 -0.51(19) . . . . ?
C6 C7 C8 C9 -0.6(2) . . . . ?
C7 C8 C9 C10 1.4(2) . . . . ?
C8 C9 C10 N3 177.07(12) . . . . ?
C8 C9 C10 C5 -0.88(19) . . . . ?
C10 N3 C2 C1 178.96(11) . . . . ?
C10 N3 C2 C3 -1.18(18) . . . . ?
C10 N3 B1 F1 65.80(16) . . . . ?
C10 N3 B1 F2 -63.53(17) . . . . ?
C10 N3 B1 N1 -177.92(11) . . . . ?
C10 C5 C6 C7 1.39(19) . . . . ?
C11 C1 C2 N3 -172.53(13) . . . . ?
C11 C1 C2 C3 7.6(2) . . . . ?
C12 C13 C14 C15 0.50(19) . . . . ?
C13 C12 C17 C16 -2.90(19) . . . . ?
C13 C14 C15 O1 178.86(11) . . . . ?
C13 C14 C15 C16 -2.25(19) . . . . ?
C14 C15 C16 C17 1.40(19) . . . . ?
C15 O1 C18 C19 168.88(11) . . . . ?
C15 C16 C17 C12 1.18(19) . . . . ?
C17 C12 C13 C14 2.03(19) . . . . ?
C18 O1 C15 C14 178.37(11) . . . . ?
C18 O1 C15 C16 -0.46(18) . . . . ?
B1 N1 N2 C12 14.3(2) . . . . ?
B1 N1 C1 C2 3.69(14) . . . . ?
B1 N1 C1 C11 177.41(12) . . . . ?
B1 N3 C2 C1 -5.43(15) . . . . ?
B1 N3 C2 C3 174.43(12) . . . . ?
B1 N3 C10 C5 -173.72(12) . . . . ?
B1 N3 C10 C9 8.30(19) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id AzoBF2-2C
_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 1.370
_oxdiff_exptl_absorpt_empirical_full_min 0.762
####################################################################### 
# 
# 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_ia423b
_database_code_depnum_ccdc_archive 'CCDC 2257908'
loop_
_audit_author_name
_audit_author_address
'Qingkai Qi'
;Dartmouth College
United States of America
;
_audit_update_record             
;
2023-04-20 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;
_audit_creation_date             2023-04-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H31 B F2 N4 O'
_chemical_formula_sum            'C27 H31 B F2 N4 O'
_chemical_formula_weight         476.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         C27H31BF2N4O
_chemical_oxdiff_usercomment     AzoBF2-10C
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'
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      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                   7.9997(3)
_cell_length_b                   11.4194(4)
_cell_length_c                   14.6997(6)
_cell_angle_alpha                72.158(3)
_cell_angle_beta                 82.260(3)
_cell_angle_gamma                72.295(3)
_cell_volume                     1216.43(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15652
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      80.1490
_cell_measurement_theta_min      3.1550
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.736
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.631
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark yellow'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             504
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0141
0 -1 0 0.0105
-1 0 0 0.2122
1 0 0 0.1953
0 1 1 0.0184
0 -1 -1 0.0350
0 0 -9 0.0371
0 0 9 0.0235
3 -1 -6 0.1205
-4 -1 4 0.1698

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.443
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.025
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0006 1.0010 0.0017 0.0437 -0.1402 -0.0156
0.0003 -1.0010 -0.0011 -0.0437 0.1402 0.0157
-1.0008 -0.0008 0.0047 -0.0802 -0.1017 0.1557
1.0008 0.0008 -0.0047 0.0802 0.1017 -0.1557
-0.0015 0.9974 1.0041 -0.0586 -0.1343 -0.0574
0.0015 -0.9974 -1.0041 0.0586 0.1343 0.0574
0.0142 0.0528 -8.9934 0.9189 -0.0552 0.3739
-0.0142 -0.0528 8.9934 -0.9189 0.0552 -0.3739
3.0164 -0.9707 -6.0219 0.8106 0.4099 -0.2022
-4.0141 -1.0244 4.0142 -0.7731 -0.2430 0.4730

_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus.  A suitable 
crystal was chosen and mounted on a nylon loop using Paratone oil.  Data  were 
measured based on the Pre-Experiment plugin of CrysAlisPro software.  Cell 
parameters were retrieved using CrysAlisPro software and data reduction was 
performed using the intergration software inside the CrysAlisPro which 
corrects for Lp.  The structure was solved by the direct method using the 
SHELXT program and refined by least squares method on F2, SHELXL,
 incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25331
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.234
_diffrn_reflns_theta_min         3.162
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  77.00   0.50    0.29    --   47.10 -93.00 120.00  176
  2  ω   -163.00 -85.00   0.50    1.16    --  -91.75 -93.00 120.00  156
  3  ω    -78.00 -19.00   0.50    1.16    --  -91.75  93.00-127.00  118
  4  ω    106.00 178.00   0.50    1.16    --  113.25  93.00-127.00  144
  5  ω     42.00 104.00   0.50    1.16    --  113.25 -93.00 120.00  124
  6  ω    -39.00  28.00   0.50    0.29    --  -47.10  19.00-150.00  134
  7  ω    -39.00  28.00   0.50    0.29    --  -47.10  19.00-120.00  134
  8  ω    -47.00  26.00   0.50    0.29    --  -47.10  37.00 150.00  146
  9  ω    -77.00  26.00   0.50    0.29    --  -47.10  93.00-127.00  206
 10  ω     36.00  93.00   0.50    0.29    --   47.10-125.00 150.00  114
 11  ω     35.00 120.00   0.50    0.29    --   47.10  37.00 -90.00  170
 12  ω    -53.00 -20.00   0.50    1.16    --  -91.75  45.00-120.00   66
 13  ω    -53.00 -20.00   0.50    1.16    --  -91.75  45.00  90.00   66
 14  ω   -163.00-106.00   0.50    1.16    --  -91.75 -61.00 150.00  114
 15  ω    -53.00 -20.00   0.50    1.16    --  -91.75  45.00 150.00   66
 16  ω   -163.00-106.00   0.50    1.16    --  -91.75 -61.00-150.00  114
 17  ω     42.00  69.00   0.50    1.16    --  113.25 -61.00-150.00   54
 18  ω     42.00 104.00   0.50    1.16    --  113.25 -94.00 -60.00  124
 19  ω     44.00 108.00   0.50    1.16    --  113.25-125.00  30.00  128
 20  ω     42.00 104.00   0.50    1.16    --  113.25 -94.00-150.00  124
 21  ω     42.00 104.00   0.50    1.16    --  113.25 -94.00-180.00  124
 22  ω     42.00  69.00   0.50    1.16    --  113.25 -61.00 -30.00   54
 23  ω     42.00  69.00   0.50    1.16    --  113.25 -61.00 -90.00   54
 24  ω     44.00 108.00   0.50    1.16    --  113.25-125.00  60.00  128
 25  ω     42.00 104.00   0.50    1.16    --  113.25 -94.00 150.00  124
 26  ω     43.00 105.00   0.50    1.16    --  113.25-104.00 -82.45  124
 27  ω    101.00 178.00   0.50    1.16    --  113.25  45.00-150.00  154
 28  ω     42.00 104.00   0.50    1.16    --  113.25 -94.00 -90.00  124
 29  ω     97.00 178.00   0.50    1.16    --  113.25 125.00 -90.00  162
 30  ω     42.00 104.00   0.50    1.16    --  113.25 -94.00-120.00  124
 31  ω     42.00 104.00   0.50    1.16    --  113.25 -94.00  60.00  124
 32  ω     42.00 104.00   0.50    1.16    --  113.25 -94.00  90.00  124
 33  ω    100.00 178.00   0.50    1.16    --  113.25  15.00-180.00  156
 34  ω    101.00 178.00   0.50    1.16    --  113.25  45.00 -30.00  154
 35  ω    101.00 178.00   0.50    1.16    --  113.25  45.00 -90.00  154
 36  ω    100.00 178.00   0.50    1.16    --  113.25  15.00 120.00  156
 37  ω     42.00  69.00   0.50    1.16    --  113.25 -61.00  60.00   54
 38  ω     44.00 108.00   0.50    1.16    --  113.25-125.00  90.00  128
 39  ω     42.00  69.00   0.50    1.16    --  113.25 -61.00  30.00   54
 40  ω    101.00 178.00   0.50    1.16    --  113.25  30.00  30.00  154
 41  ω    100.00 178.00   0.50    1.16    --  113.25  15.00 -60.00  156
 42  ω     42.00  69.00   0.50    1.16    --  113.25 -61.00 -60.00   54
 43  ω     42.00  94.00   0.50    1.16    --  113.25 -77.00 -30.00  104
 44  ω     42.00  69.00   0.50    1.16    --  113.25 -61.00  90.00   54
 45  ω    100.00 178.00   0.50    1.16    --  113.25  15.00-150.00  156
 46  ω     42.00  69.00   0.50    1.16    --  113.25 -61.00-180.00   54
 47  ω    110.00 178.00   0.50    1.16    --  113.25  77.00-150.00  136
 48  ω     42.00  69.00   0.50    1.16    --  113.25 -61.00   0.00   54
 49  ω   -118.00 -34.00   0.50    0.29    --  -47.10 -46.00  49.27  168
 50  ω   -119.00 -35.00   0.50    0.29    --  -47.10 -43.00 -53.74  168
 51  ω   -118.00 -51.00   0.50    0.29    --  -47.10 -46.00-137.18  134
 52  ω   -119.00 -34.00   0.50    0.29    --  -47.10 -45.00 142.90  170
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0796314000
_diffrn_orient_matrix_UB_12      0.0438382000
_diffrn_orient_matrix_UB_13      -0.1017866000
_diffrn_orient_matrix_UB_21      0.1017465000
_diffrn_orient_matrix_UB_22      -0.1400372000
_diffrn_orient_matrix_UB_23      0.0054744000
_diffrn_orient_matrix_UB_31      -0.1557495000
_diffrn_orient_matrix_UB_32      -0.0156387000
_diffrn_orient_matrix_UB_33      -0.0419103000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4543
_reflns_number_total             5193
_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 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.103
_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)+(0.0545P)²+0.2589P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1059
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_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:
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,
 H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C16(H16),
 C17(H17)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_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 1.05746(8) 0.19609(6) 0.87999(5) 0.02051(15) Uani 1 1 d . . . . .
F2 F 1.17227(8) 0.29025(6) 0.73482(4) 0.02049(15) Uani 1 1 d . . . . .
O1 O 0.34574(10) 0.52462(8) 0.65225(6) 0.02305(18) Uani 1 1 d . . . . .
N1 N 1.06885(11) 0.41787(9) 0.85105(6) 0.01693(19) Uani 1 1 d . . . . .
N2 N 0.91895(12) 0.50398(9) 0.83637(7) 0.01869(19) Uani 1 1 d . . . . .
N3 N 1.33534(11) 0.24496(9) 0.87452(7) 0.01729(19) Uani 1 1 d . . . . .
N4 N 1.14408(13) 0.64975(10) 0.93885(8) 0.0261(2) Uani 1 1 d . . . . .
C1 C 1.19100(14) 0.44042(10) 0.89572(8) 0.0179(2) Uani 1 1 d . . . . .
C2 C 1.34674(13) 0.33803(10) 0.90950(7) 0.0173(2) Uani 1 1 d . . . . .
C3 C 1.50040(14) 0.32685(11) 0.95320(8) 0.0193(2) Uani 1 1 d . . . . .
H3 H 1.507071 0.392532 0.978388 0.023 Uiso 1 1 calc R U . . .
C4 C 1.63828(14) 0.22031(11) 0.95844(8) 0.0206(2) Uani 1 1 d . . . . .
H4 H 1.742221 0.211994 0.987284 0.025 Uiso 1 1 calc R U . . .
C5 C 1.62898(14) 0.12097(11) 0.92124(8) 0.0189(2) Uani 1 1 d . . . . .
C6 C 1.76762(14) 0.00811(11) 0.92666(8) 0.0223(2) Uani 1 1 d . . . . .
H6 H 1.872888 -0.003155 0.955512 0.027 Uiso 1 1 calc R U . . .
C7 C 1.75231(15) -0.08564(11) 0.89075(8) 0.0235(2) Uani 1 1 d . . . . .
H7 H 1.845744 -0.161883 0.895541 0.028 Uiso 1 1 calc R U . . .
C8 C 1.59771(15) -0.06817(11) 0.84689(8) 0.0224(2) Uani 1 1 d . . . . .
H8 H 1.588539 -0.132591 0.821043 0.027 Uiso 1 1 calc R U . . .
C9 C 1.45869(14) 0.04070(11) 0.84054(8) 0.0201(2) Uani 1 1 d . . . . .
H9 H 1.354669 0.050968 0.810941 0.024 Uiso 1 1 calc R U . . .
C10 C 1.47298(13) 0.13585(10) 0.87831(8) 0.0173(2) Uani 1 1 d . . . . .
C11 C 1.16249(13) 0.55568(11) 0.92025(8) 0.0198(2) Uani 1 1 d . . . . .
C12 C 0.78444(14) 0.49394(10) 0.79061(8) 0.0181(2) Uani 1 1 d . . . . .
C13 C 0.63232(14) 0.59611(10) 0.79014(8) 0.0206(2) Uani 1 1 d . . . . .
H13 H 0.632438 0.657477 0.821521 0.025 Uiso 1 1 calc R U . . .
C14 C 0.48226(14) 0.61073(11) 0.74568(8) 0.0212(2) Uani 1 1 d . . . . .
H14 H 0.381415 0.680814 0.746585 0.025 Uiso 1 1 calc R U . . .
C15 C 0.48183(14) 0.52093(10) 0.69965(8) 0.0195(2) Uani 1 1 d . . . . .
C16 C 0.63100(14) 0.41684(11) 0.70088(8) 0.0205(2) Uani 1 1 d . . . . .
H16 H 0.629169 0.354793 0.670561 0.025 Uiso 1 1 calc R U . . .
C17 C 0.78017(14) 0.40258(11) 0.74511(8) 0.0200(2) Uani 1 1 d . . . . .
H17 H 0.879876 0.331448 0.744983 0.024 Uiso 1 1 calc R U . . .
C18 C 0.19315(14) 0.63360(11) 0.64195(8) 0.0207(2) Uani 1 1 d . . . . .
H18A H 0.226457 0.713670 0.609724 0.025 Uiso 1 1 calc R U . . .
H18B H 0.137282 0.638742 0.705462 0.025 Uiso 1 1 calc R U . . .
C19 C 0.06808(14) 0.61541(11) 0.58244(8) 0.0210(2) Uani 1 1 d . . . . .
H19A H 0.039367 0.533569 0.614571 0.025 Uiso 1 1 calc R U . . .
H19B H 0.126075 0.610219 0.519338 0.025 Uiso 1 1 calc R U . . .
C20 C -0.10145(14) 0.72506(11) 0.56783(8) 0.0205(2) Uani 1 1 d . . . . .
H20A H -0.157931 0.731248 0.631036 0.025 Uiso 1 1 calc R U . . .
H20B H -0.072609 0.806613 0.534720 0.025 Uiso 1 1 calc R U . . .
C21 C -0.23059(14) 0.70672(11) 0.50935(8) 0.0210(2) Uani 1 1 d . . . . .
H21A H -0.173343 0.699367 0.446520 0.025 Uiso 1 1 calc R U . . .
H21B H -0.260212 0.625575 0.542892 0.025 Uiso 1 1 calc R U . . .
C22 C -0.39953(14) 0.81641(11) 0.49331(8) 0.0215(2) Uani 1 1 d . . . . .
H22A H -0.369466 0.897761 0.461235 0.026 Uiso 1 1 calc R U . . .
H22B H -0.457951 0.822414 0.556175 0.026 Uiso 1 1 calc R U . . .
C23 C -0.52795(14) 0.80053(11) 0.43290(8) 0.0207(2) Uani 1 1 d . . . . .
H23A H -0.563928 0.721958 0.466717 0.025 Uiso 1 1 calc R U . . .
H23B H -0.467841 0.789704 0.371361 0.025 Uiso 1 1 calc R U . . .
C24 C -0.69163(14) 0.91499(11) 0.41291(8) 0.0217(2) Uani 1 1 d . . . . .
H24A H -0.747932 0.927725 0.474704 0.026 Uiso 1 1 calc R U . . .
H24B H -0.654962 0.992705 0.377261 0.026 Uiso 1 1 calc R U . . .
C25 C -0.82712(14) 0.90140(11) 0.35603(8) 0.0202(2) Uani 1 1 d . . . . .
H25A H -0.866032 0.824735 0.391894 0.024 Uiso 1 1 calc R U . . .
H25B H -0.771427 0.888121 0.294267 0.024 Uiso 1 1 calc R U . . .
C26 C -0.98743(14) 1.01862(11) 0.33665(9) 0.0233(2) Uani 1 1 d . . . . .
H26A H -1.041397 1.032985 0.398413 0.028 Uiso 1 1 calc R U . . .
H26B H -0.948627 1.094927 0.299642 0.028 Uiso 1 1 calc R U . . .
C27 C -1.12523(15) 1.00469(12) 0.28168(9) 0.0274(3) Uani 1 1 d . . . . .
H27A H -1.074762 0.995590 0.218822 0.041 Uiso 1 1 calc R U . . .
H27B H -1.226446 1.080871 0.273357 0.041 Uiso 1 1 calc R U . . .
H27C H -1.163166 0.928645 0.317485 0.041 Uiso 1 1 calc R U . . .
B1 B 1.15374(15) 0.27816(11) 0.83059(9) 0.0170(2) 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 1.3675(14) . ?
F2 B1 1.3637(14) . ?
O1 C15 1.3531(13) . ?
O1 C18 1.4395(12) . ?
N1 N2 1.2938(12) . ?
N1 C1 1.3718(14) . ?
N1 B1 1.6362(14) . ?
N2 C12 1.3931(14) . ?
N3 C2 1.3449(14) . ?
N3 C10 1.3811(13) . ?
N3 B1 1.5617(14) . ?
N4 C11 1.1503(15) . ?
C1 C2 1.4133(14) . ?
C1 C11 1.4144(15) . ?
C2 C3 1.4166(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.3608(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.4261(16) . ?
C5 C6 1.4103(15) . ?
C5 C10 1.4149(15) . ?
C6 H6 0.9500 . ?
C6 C7 1.3722(17) . ?
C7 H7 0.9500 . ?
C7 C8 1.4039(16) . ?
C8 H8 0.9500 . ?
C8 C9 1.3809(15) . ?
C9 H9 0.9500 . ?
C9 C10 1.4015(15) . ?
C12 C13 1.4057(14) . ?
C12 C17 1.4114(16) . ?
C13 H13 0.9500 . ?
C13 C14 1.3852(15) . ?
C14 H14 0.9500 . ?
C14 C15 1.3918(16) . ?
C15 C16 1.4026(15) . ?
C16 H16 0.9500 . ?
C16 C17 1.3781(15) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5109(15) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.5278(14) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.5267(14) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.5252(14) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.5279(15) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.5286(14) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.5244(15) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.5291(14) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.5228(15) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O1 C18 118.46(9) . . ?
N2 N1 C1 117.36(9) . . ?
N2 N1 B1 134.73(9) . . ?
C1 N1 B1 107.90(8) . . ?
N1 N2 C12 123.22(9) . . ?
C2 N3 C10 121.66(9) . . ?
C2 N3 B1 111.80(9) . . ?
C10 N3 B1 126.54(9) . . ?
N1 C1 C2 111.71(9) . . ?
N1 C1 C11 122.65(9) . . ?
C2 C1 C11 125.59(10) . . ?
N3 C2 C1 111.09(9) . . ?
N3 C2 C3 121.05(10) . . ?
C1 C2 C3 127.86(10) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.80(10) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 120.94(10) . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 122.76(10) . . ?
C6 C5 C10 118.80(10) . . ?
C10 C5 C4 118.44(10) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.80(10) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.59(10) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.37(11) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.18(10) . . ?
C10 C9 H9 120.4 . . ?
N3 C10 C5 119.10(10) . . ?
N3 C10 C9 120.65(9) . . ?
C9 C10 C5 120.25(10) . . ?
N4 C11 C1 177.94(12) . . ?
N2 C12 C13 111.32(9) . . ?
N2 C12 C17 130.90(10) . . ?
C13 C12 C17 117.76(10) . . ?
C12 C13 H13 118.7 . . ?
C14 C13 C12 122.52(10) . . ?
C14 C13 H13 118.7 . . ?
C13 C14 H14 120.6 . . ?
C13 C14 C15 118.83(10) . . ?
C15 C14 H14 120.6 . . ?
O1 C15 C14 125.04(10) . . ?
O1 C15 C16 115.39(10) . . ?
C14 C15 C16 119.58(10) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.45(10) . . ?
C17 C16 H16 119.3 . . ?
C12 C17 H17 120.1 . . ?
C16 C17 C12 119.83(10) . . ?
C16 C17 H17 120.1 . . ?
O1 C18 H18A 110.3 . . ?
O1 C18 H18B 110.3 . . ?
O1 C18 C19 106.95(9) . . ?
H18A C18 H18B 108.6 . . ?
C19 C18 H18A 110.3 . . ?
C19 C18 H18B 110.3 . . ?
C18 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
C18 C19 C20 111.77(9) . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C19 C20 H20A 109.1 . . ?
C19 C20 H20B 109.1 . . ?
H20A C20 H20B 107.9 . . ?
C21 C20 C19 112.36(9) . . ?
C21 C20 H20A 109.1 . . ?
C21 C20 H20B 109.1 . . ?
C20 C21 H21A 109.0 . . ?
C20 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C22 C21 C20 112.84(9) . . ?
C22 C21 H21A 109.0 . . ?
C22 C21 H21B 109.0 . . ?
C21 C22 H22A 108.9 . . ?
C21 C22 H22B 108.9 . . ?
C21 C22 C23 113.27(9) . . ?
H22A C22 H22B 107.7 . . ?
C23 C22 H22A 108.9 . . ?
C23 C22 H22B 108.9 . . ?
C22 C23 H23A 109.1 . . ?
C22 C23 H23B 109.1 . . ?
C22 C23 C24 112.42(9) . . ?
H23A C23 H23B 107.9 . . ?
C24 C23 H23A 109.1 . . ?
C24 C23 H23B 109.1 . . ?
C23 C24 H24A 108.7 . . ?
C23 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C25 C24 C23 114.40(9) . . ?
C25 C24 H24A 108.7 . . ?
C25 C24 H24B 108.7 . . ?
C24 C25 H25A 109.1 . . ?
C24 C25 H25B 109.1 . . ?
C24 C25 C26 112.62(9) . . ?
H25A C25 H25B 107.8 . . ?
C26 C25 H25A 109.1 . . ?
C26 C25 H25B 109.1 . . ?
C25 C26 H26A 109.0 . . ?
C25 C26 H26B 109.0 . . ?
H26A C26 H26B 107.8 . . ?
C27 C26 C25 112.97(9) . . ?
C27 C26 H26A 109.0 . . ?
C27 C26 H26B 109.0 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
F1 B1 N1 109.94(8) . . ?
F1 B1 N3 112.42(9) . . ?
F2 B1 F1 113.54(9) . . ?
F2 B1 N1 111.04(9) . . ?
F2 B1 N3 111.31(9) . . ?
N3 B1 N1 97.50(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C15 C16 C17 178.80(10) . . . . ?
O1 C18 C19 C20 179.12(9) . . . . ?
N1 N2 C12 C13 175.89(9) . . . . ?
N1 N2 C12 C17 -5.71(18) . . . . ?
N1 C1 C2 N3 0.43(13) . . . . ?
N1 C1 C2 C3 -179.71(10) . . . . ?
N2 N1 C1 C2 178.55(9) . . . . ?
N2 N1 C1 C11 -3.91(15) . . . . ?
N2 N1 B1 F1 -61.32(15) . . . . ?
N2 N1 B1 F2 65.18(15) . . . . ?
N2 N1 B1 N3 -178.50(11) . . . . ?
N2 C12 C13 C14 177.46(10) . . . . ?
N2 C12 C17 C16 -177.23(11) . . . . ?
N3 C2 C3 C4 0.70(16) . . . . ?
C1 N1 N2 C12 179.06(9) . . . . ?
C1 N1 B1 F1 117.05(9) . . . . ?
C1 N1 B1 F2 -116.46(9) . . . . ?
C1 N1 B1 N3 -0.14(10) . . . . ?
C1 C2 C3 C4 -179.15(10) . . . . ?
C2 N3 C10 C5 0.85(15) . . . . ?
C2 N3 C10 C9 -179.37(10) . . . . ?
C2 N3 B1 F1 -114.83(10) . . . . ?
C2 N3 B1 F2 116.50(10) . . . . ?
C2 N3 B1 N1 0.40(10) . . . . ?
C2 C3 C4 C5 -0.33(16) . . . . ?
C3 C4 C5 C6 -178.89(10) . . . . ?
C3 C4 C5 C10 0.23(16) . . . . ?
C4 C5 C6 C7 179.34(11) . . . . ?
C4 C5 C10 N3 -0.47(15) . . . . ?
C4 C5 C10 C9 179.75(10) . . . . ?
C5 C6 C7 C8 0.90(17) . . . . ?
C6 C5 C10 N3 178.69(10) . . . . ?
C6 C5 C10 C9 -1.09(16) . . . . ?
C6 C7 C8 C9 -1.19(17) . . . . ?
C7 C8 C9 C10 0.32(17) . . . . ?
C8 C9 C10 N3 -178.95(10) . . . . ?
C8 C9 C10 C5 0.82(16) . . . . ?
C10 N3 C2 C1 178.90(9) . . . . ?
C10 N3 C2 C3 -0.98(16) . . . . ?
C10 N3 B1 F1 65.77(13) . . . . ?
C10 N3 B1 F2 -62.89(13) . . . . ?
C10 N3 B1 N1 -178.99(9) . . . . ?
C10 C5 C6 C7 0.22(16) . . . . ?
C11 C1 C2 N3 -177.03(10) . . . . ?
C11 C1 C2 C3 2.83(18) . . . . ?
C12 C13 C14 C15 -0.01(17) . . . . ?
C13 C12 C17 C16 1.09(16) . . . . ?
C13 C14 C15 O1 -178.90(10) . . . . ?
C13 C14 C15 C16 1.27(17) . . . . ?
C14 C15 C16 C17 -1.36(17) . . . . ?
C15 O1 C18 C19 177.14(9) . . . . ?
C15 C16 C17 C12 0.14(17) . . . . ?
C17 C12 C13 C14 -1.17(17) . . . . ?
C18 O1 C15 C14 4.68(16) . . . . ?
C18 O1 C15 C16 -175.49(9) . . . . ?
C18 C19 C20 C21 -178.94(9) . . . . ?
C19 C20 C21 C22 -179.33(9) . . . . ?
C20 C21 C22 C23 178.68(9) . . . . ?
C21 C22 C23 C24 -176.74(9) . . . . ?
C22 C23 C24 C25 -177.78(9) . . . . ?
C23 C24 C25 C26 -179.30(9) . . . . ?
C24 C25 C26 C27 -178.78(10) . . . . ?
B1 N1 N2 C12 -2.70(18) . . . . ?
B1 N1 C1 C2 -0.14(12) . . . . ?
B1 N1 C1 C11 177.41(10) . . . . ?
B1 N3 C2 C1 -0.53(12) . . . . ?
B1 N3 C2 C3 179.60(9) . . . . ?
B1 N3 C10 C5 -179.81(9) . . . . ?
B1 N3 C10 C9 -0.03(16) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id AzoBF2-10C
_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 1.504
_oxdiff_exptl_absorpt_empirical_full_min 0.754
####################################################################### 
# 
# 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_ia423e
_database_code_depnum_ccdc_archive 'CCDC 2257910'
loop_
_audit_author_name
_audit_author_address
'Qingkai Qi'
;Dartmouth College
United States of America
;
_audit_update_record             
;
2023-04-20 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;
_audit_creation_date             2023-04-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'0.5(C29 H35 B F2 N4 O2), 0.5(C29 H33 B F2 N4 O2)'
_chemical_formula_sum            'C29 H34 B F2 N4 O2'
_chemical_formula_weight         519.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O FB'
_chemical_oxdiff_usercomment     AZOBF2-di6C
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'
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      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                   7.2509(3)
_cell_length_b                   41.2972(9)
_cell_length_c                   9.7380(2)
_cell_angle_alpha                90.122(2)
_cell_angle_beta                 109.885(3)
_cell_angle_gamma                89.203(3)
_cell_volume                     2741.83(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18354
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      79.7850
_cell_measurement_theta_min      3.1830
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.732
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.358
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.80a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1100
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 2 0.0635
0 -1 0 0.0076
0 1 0 0.0208
-1 7 -5 0.0523
5 -8 -2 0.2238
-3 8 3 0.1557

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.03
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0035 -0.9846 2.0017 -0.0394 -0.0458 -0.3337
0.0023 -0.9979 -0.0005 0.0284 -0.0237 -0.0044
-0.0023 0.9979 0.0005 -0.0284 0.0237 0.0044
-0.6194 6.9164 -5.0035 0.0565 0.3236 0.8770
5.1173 -7.6947 -1.9935 -0.4342 -1.0385 0.0989
-2.6169 7.8492 3.0010 0.0427 0.6003 -0.3592

_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus.  A suitable 
crystal was chosen and mounted on a nylon loop using Paratone oil.  Data  were 
measured based on the Pre-Experiment plugin of CrysAlisPro software.  Cell 
parameters were retrieved using CrysAlisPro software and data reduction was 
performed using the intergration software inside the CrysAlisPro which 
corrects for Lp.  The structure was solved by the direct method using the 
SHELXT program and refined by least squares method on F2, SHELXL,
 incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0870
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_k_min       -52
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            51198
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.555
_diffrn_reflns_theta_min         3.211
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -118.00 -55.00   0.50    1.72    --  -46.85-155.00 120.00  126
  2  ω    -82.00 -11.00   0.50    1.72    --  -46.85 120.00   2.00  142
  3  ω   -103.00 -30.00   0.50    1.72    --  -46.85 155.00 159.00  146
  4  ω     33.00  90.00   0.50    1.72    --   46.85-120.00 -82.00  114
  5  ω     52.00 114.00   0.50    1.72    --   46.85-155.00 120.00  124
  6  ω   -141.00 -55.00   0.50    6.89    --  -91.75-155.00 120.00  172
  7  ω   -161.00 -79.00   0.50    6.89    --  -91.75-120.00 -82.00  164
  8  ω   -103.00 -30.00   0.50    6.89    --  -91.75 155.00 159.00  146
  9  ω    -82.00 -22.00   0.50    6.89    --  -91.75 120.00   2.00  120
 10  ω    100.00 178.00   0.50    6.89    --  113.25 120.00   2.00  156
 11  ω     52.00 123.50   0.50    6.89    --  113.25-155.00 120.00  143
 12  ω     44.00 107.00   0.50    6.89    --  113.25-120.00 -82.00  126
 13  ω     77.00 159.00   0.50    6.89    --  113.25 155.00 159.00  164
 14  ω   -118.00 -34.00   0.50    1.72    --  -46.85 -46.00  14.74  168
 15  ω    -39.00  29.00   0.50    1.72    --  -46.85  19.00 -60.00  136
 16  ω    -39.00  29.00   0.50    1.72    --  -46.85  19.00-180.00  136
 17  ω   -120.00 -34.00   0.50    1.72    --  -46.85 -37.00 150.00  172
 18  ω    -27.00  38.00   0.50    1.72    --   46.85 -19.00 -60.00  130
 19  ω     36.00  93.00   0.50    1.72    --   46.85-125.00-150.00  114
 20  ω   -163.00 -82.00   0.50    6.89    --  -91.75 -47.00 -19.40  162
 21  ω    -53.00 -20.00   0.50    6.89    --  -91.75  45.00 -30.00   66
 22  ω     42.00  69.00   0.50    6.89    --  113.25 -61.00 150.00   54
 23  ω     42.00 104.00   0.50    6.89    --  113.25 -94.00 -90.00  124
 24  ω     44.00 108.00   0.50    6.89    --  113.25-125.00  30.00  128
 25  ω    106.00 178.00   0.50    6.89    --  113.25  61.00 120.00  144
 26  ω     42.00  69.00   0.50    6.89    --  113.25 -61.00 -90.00   54
 27  ω    110.00 178.00   0.50    6.89    --  113.25  77.00-120.00  136
 28  ω     42.00  69.00   0.50    6.89    --  113.25 -61.00  60.00   54
 29  ω     44.00 108.00   0.50    6.89    --  113.25-125.00-120.00  128
 30  ω    101.00 178.00   0.50    6.89    --  113.25  45.00-180.00  154
 31  ω     42.00  69.00   0.50    6.89    --  113.25 -61.00-180.00   54
 32  ω     42.00 104.00   0.50    6.89    --  113.25 -94.00 120.00  124
 33  ω    110.00 178.00   0.50    6.89    --  113.25  77.00 -90.00  136
 34  ω     42.00 104.00   0.50    6.89    --  113.25 -94.00 150.00  124
 35  ω     42.00  99.50   0.50    6.89    --  113.25 -94.00  90.00  115
 36  ω     42.00  94.00   0.50    6.89    --  113.25 -77.00   0.00  104
 37  ω     42.00  94.00   0.50    6.89    --  113.25 -77.00  30.00  104
 38  ω     42.00  94.00   0.50    6.89    --  113.25 -77.00 -90.00  104
 39  ω     42.00 104.00   0.50    6.89    --  113.25 -94.00-150.00  124
 40  ω     42.00  69.00   0.50    6.89    --  113.25 -61.00  90.00   54
 41  ω    106.00 178.00   0.50    6.89    --  113.25  61.00  60.00  144
 42  ω     42.00  69.00   0.50    6.89    --  113.25 -61.00 -30.00   54
 43  ω    101.00 178.00   0.50    6.89    --  113.25  45.00-120.00  154
 44  ω    101.00 164.00   0.50    6.89    --  113.25  45.00 -60.00  126
 45  ω     45.00  87.00   0.50    6.89    --  113.25 -77.00  60.00   84
 46  ω     42.00  67.00   0.50    6.89    --  113.25 -61.00-150.00   50
 47  ω     78.00 104.00   0.50    6.89    --  113.25 -99.00 178.07   52
 48  ω     43.00  72.00   0.50    6.89    --  113.25 -94.00 -30.00   58
 49  ω     76.00 102.00   0.50    6.89    --  113.25 -94.00 -30.00   52
 50  ω     59.00  94.00   0.50    6.89    --  113.25 -94.00  30.00   70
 51  ω    101.00 156.00   0.50    6.89    --  113.25  30.00  60.00  110
 52  ω     46.00  72.00   0.50    6.89    --  113.25 -77.00-150.00   52
 53  ω     71.00 104.00   0.50    6.89    --  113.25 -82.00 -73.97   66
 54  ω    101.00 178.00   0.50    6.89    --  113.25  48.00 165.52  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1412268641
_diffrn_orient_matrix_UB_12      -0.0287875810
_diffrn_orient_matrix_UB_13      -0.0336136708
_diffrn_orient_matrix_UB_21      -0.1722183673
_diffrn_orient_matrix_UB_22      0.0233171896
_diffrn_orient_matrix_UB_23      -0.0111171957
_diffrn_orient_matrix_UB_31      -0.0381106588
_diffrn_orient_matrix_UB_32      0.0044129794
_diffrn_orient_matrix_UB_33      -0.1644639508
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9165
_reflns_number_total             11633
_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 1.171.42.80a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.80a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.80a (Rigaku OD, 2023)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.074
_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     689
_refine_ls_number_reflns         11633
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0783
_refine_ls_restrained_S_all      1.049
_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)+(0.1385P)²+1.5448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2231
_refine_ls_wR_factor_ref         0.2356
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_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:
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,
 H22B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B),
 C28(H28A,H28B), C18A(H18C,H18D), C19A(H19C,H19D), C20A(H20C,H20D), C21A(H21C,
 H21D), C22A(H22C,H22D), C24A(H24C,H24D), C26A(H26C,H26D), C27A(H27C,H27D),
 C28A(H28C,H28D)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C8(H8), C9(H9), C13(H13), C14(H14), C16(H16),
 C17(H17), C3A(H3A), C4A(H4A), C6A(H6A), C8A(H8A), C9A(H9A), C13A(H13A),
 C14A(H14A), C16A(H16A), C17A(H17A)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C29(H29A,H29B,H29C), C23A(H23D,H23E,H23F), C29A(H29D,
 H29E,H29F)
;
_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 -0.1069(2) 0.90785(4) -0.01099(16) 0.0406(3) Uani 1 1 d . . . . .
F2 F -0.3910(2) 0.90908(4) 0.04094(15) 0.0411(3) Uani 1 1 d . . . . .
O1 O -0.3496(3) 0.75493(4) -0.17463(19) 0.0415(4) Uani 1 1 d . . . . .
O2 O 0.0264(3) 1.04705(5) 0.37722(19) 0.0417(4) Uani 1 1 d . . . . .
N1 N -0.4175(3) 0.91187(5) -0.2199(2) 0.0357(4) Uani 1 1 d . . . . .
N2 N -0.4692(3) 0.88578(5) -0.2978(2) 0.0375(4) Uani 1 1 d . . . . .
N3 N -0.3026(3) 0.95765(5) -0.0608(2) 0.0346(4) Uani 1 1 d . . . . .
N4 N -0.6633(4) 0.94554(5) -0.5658(2) 0.0447(5) Uani 1 1 d . . . . .
C1 C -0.4716(4) 0.94030(6) -0.2911(3) 0.0354(5) Uani 1 1 d . . . . .
C2 C -0.4058(3) 0.96735(6) -0.1981(3) 0.0344(5) Uani 1 1 d . . . . .
C3 C -0.4357(4) 1.00006(6) -0.2363(3) 0.0368(5) Uani 1 1 d . . . . .
H3 H -0.508876 1.006320 -0.333717 0.044 Uiso 1 1 calc R U . . .
C4 C -0.3583(4) 1.02287(6) -0.1321(3) 0.0380(5) Uani 1 1 d . . . . .
H4 H -0.377916 1.045206 -0.156692 0.046 Uiso 1 1 calc R U . . .
C5 C -0.2477(3) 1.01335(6) 0.0144(3) 0.0351(5) Uani 1 1 d . . . . .
C6 C -0.1660(4) 1.03664(6) 0.1237(3) 0.0372(5) Uani 1 1 d . . . . .
H6 H -0.184102 1.059087 0.101098 0.045 Uiso 1 1 calc R U . . .
C7 C -0.0596(4) 1.02657(6) 0.2636(3) 0.0377(5) Uani 1 1 d . . . . .
C8 C -0.0332(4) 0.99347(7) 0.2963(3) 0.0389(5) Uani 1 1 d . . . . .
H8 H 0.039839 0.986872 0.393168 0.047 Uiso 1 1 calc R U . . .
C9 C -0.1105(4) 0.97023(6) 0.1916(3) 0.0371(5) Uani 1 1 d . . . . .
H9 H -0.089402 0.947877 0.215446 0.045 Uiso 1 1 calc R U . . .
C10 C -0.2212(3) 0.98014(6) 0.0485(3) 0.0348(5) Uani 1 1 d . . . . .
C11 C -0.5769(4) 0.94269(6) -0.4423(3) 0.0374(5) Uani 1 1 d . . . . .
C12 C -0.4235(4) 0.85443(6) -0.2438(3) 0.0369(5) Uani 1 1 d . . . . .
C13 C -0.4884(4) 0.83145(7) -0.3569(3) 0.0416(6) Uani 1 1 d . . . . .
H13 H -0.552917 0.838742 -0.454184 0.050 Uiso 1 1 calc R U . . .
C14 C -0.4606(4) 0.79892(7) -0.3299(3) 0.0426(6) Uani 1 1 d . . . . .
H14 H -0.504971 0.784009 -0.408326 0.051 Uiso 1 1 calc R U . . .
C15 C -0.3678(4) 0.78751(6) -0.1881(3) 0.0377(5) Uani 1 1 d . . . . .
C16 C -0.3026(4) 0.80980(6) -0.0735(3) 0.0373(5) Uani 1 1 d . . . . .
H16 H -0.239642 0.802268 0.023581 0.045 Uiso 1 1 calc R U . . .
C17 C -0.3295(4) 0.84288(6) -0.1012(3) 0.0379(5) Uani 1 1 d . . . . .
H17 H -0.283870 0.857791 -0.022839 0.045 Uiso 1 1 calc R U . . .
C18 C -0.2731(4) 0.74028(6) -0.0319(3) 0.0392(5) Uani 1 1 d . . . . .
H18A H -0.347356 0.748114 0.030490 0.047 Uiso 1 1 calc R U . . .
H18B H -0.133307 0.745772 0.015801 0.047 Uiso 1 1 calc R U . . .
C19 C -0.2952(4) 0.70412(6) -0.0539(3) 0.0375(5) Uani 1 1 d . . . . .
H19A H -0.218660 0.696758 -0.115492 0.045 Uiso 1 1 calc R U . . .
H19B H -0.434762 0.699271 -0.106683 0.045 Uiso 1 1 calc R U . . .
C20 C -0.2260(4) 0.68539(6) 0.0892(3) 0.0390(5) Uani 1 1 d . . . . .
H20A H -0.301141 0.692985 0.151411 0.047 Uiso 1 1 calc R U . . .
H20B H -0.085896 0.689978 0.141296 0.047 Uiso 1 1 calc R U . . .
C21 C -0.2511(4) 0.64891(6) 0.0672(3) 0.0393(5) Uani 1 1 d . . . . .
H21A H -0.180609 0.641587 0.001456 0.047 Uiso 1 1 calc R U . . .
H21B H -0.391998 0.644381 0.018216 0.047 Uiso 1 1 calc R U . . .
C22 C -0.1757(4) 0.62924(7) 0.2087(3) 0.0452(6) Uani 1 1 d . . . . .
H22A H -0.188280 0.605904 0.184346 0.054 Uiso 1 1 calc R U . . .
H22B H -0.034691 0.633676 0.257672 0.054 Uiso 1 1 calc R U . . .
C23 C -0.2841(6) 0.63665(7) 0.3141(3) 0.0542(7) Uani 1 1 d . . . . .
H23A H -0.423331 0.631692 0.267586 0.081 Uiso 1 1 calc R U . . .
H23B H -0.270370 0.659633 0.340340 0.081 Uiso 1 1 calc R U . . .
H23C H -0.228579 0.623409 0.402346 0.081 Uiso 1 1 calc R U . . .
C24 C -0.0067(4) 1.08089(6) 0.3474(3) 0.0399(5) Uani 1 1 d . . . . .
H24A H -0.149386 1.085688 0.312312 0.048 Uiso 1 1 calc R U . . .
H24B H 0.045325 1.087149 0.269683 0.048 Uiso 1 1 calc R U . . .
C25 C 0.0933(4) 1.10029(7) 0.4840(3) 0.0439(6) Uani 1 1 d . . . . .
H25A H 0.236757 1.096395 0.516773 0.053 Uiso 1 1 calc R U . . .
H25B H 0.045444 1.093499 0.563284 0.053 Uiso 1 1 calc R U . . .
C26 C 0.0479(4) 1.13594(7) 0.4506(3) 0.0443(6) Uani 1 1 d . . . . .
H26A H -0.095856 1.139277 0.420781 0.053 Uiso 1 1 calc R U . . .
H26B H 0.087374 1.141692 0.365958 0.053 Uiso 1 1 calc R U . . .
C27 C 0.1458(5) 1.15917(7) 0.5742(3) 0.0500(7) Uani 1 1 d . . . . .
H27A H 0.289729 1.155808 0.606477 0.060 Uiso 1 1 calc R U . . .
H27B H 0.102624 1.154369 0.658078 0.060 Uiso 1 1 calc R U . . .
C28 C 0.0964(5) 1.19466(8) 0.5283(3) 0.0552(7) Uani 1 1 d . . . . .
H28A H 0.129338 1.198825 0.439333 0.066 Uiso 1 1 calc R U . . .
H28B H -0.046503 1.198297 0.503388 0.066 Uiso 1 1 calc R U . . .
C29 C 0.2043(7) 1.21854(10) 0.6452(4) 0.0793(12) Uani 1 1 d . . . . .
H29A H 0.173906 1.240644 0.607057 0.119 Uiso 1 1 calc R U . . .
H29B H 0.345861 1.214457 0.673853 0.119 Uiso 1 1 calc R U . . .
H29C H 0.162987 1.215971 0.730472 0.119 Uiso 1 1 calc R U . . .
B1 B -0.2931(4) 0.91982(7) -0.0470(3) 0.0355(6) Uani 1 1 d . . . . .
F1A F 0.1150(2) 0.58202(3) 0.06133(15) 0.0391(3) Uani 1 1 d . . . . .
F2A F 0.3978(2) 0.58470(3) 0.00829(15) 0.0384(3) Uani 1 1 d . . . . .
O1A O 0.2419(3) 0.73467(4) -0.0255(2) 0.0431(4) Uani 1 1 d . . . . .
O2A O 0.5368(3) 0.43972(5) 0.3450(2) 0.0427(4) Uani 1 1 d . . . . .
N1A N 0.0823(3) 0.58518(5) -0.2002(2) 0.0360(4) Uani 1 1 d . . . . .
N2A N 0.0340(3) 0.61283(5) -0.2646(2) 0.0381(5) Uani 1 1 d . . . . .
N3A N 0.2000(3) 0.53615(5) -0.0598(2) 0.0350(4) Uani 1 1 d . . . . .
N4A N -0.2000(4) 0.55751(6) -0.5512(3) 0.0484(6) Uani 1 1 d . . . . .
C1A C 0.0166(4) 0.55790(6) -0.2808(3) 0.0367(5) Uani 1 1 d . . . . .
C2A C 0.0837(3) 0.52935(6) -0.1981(3) 0.0353(5) Uani 1 1 d . . . . .
C3A C 0.0431(4) 0.49707(6) -0.2442(3) 0.0372(5) Uani 1 1 d . . . . .
H3A H -0.036398 0.492414 -0.341823 0.045 Uiso 1 1 calc R U . . .
C4A C 0.1189(4) 0.47278(6) -0.1475(3) 0.0371(5) Uani 1 1 d . . . . .
H4A H 0.090413 0.450977 -0.177637 0.044 Uiso 1 1 calc R U . . .
C5A C 0.2413(3) 0.47935(6) -0.0005(3) 0.0356(5) Uani 1 1 d . . . . .
C6A C 0.3219(4) 0.45437(6) 0.1009(3) 0.0374(5) Uani 1 1 d . . . . .
H6A H 0.291386 0.432440 0.074097 0.045 Uiso 1 1 calc R U . . .
C7A C 0.4459(4) 0.46185(6) 0.2400(3) 0.0384(5) Uani 1 1 d . . . . .
C8A C 0.4871(4) 0.49451(7) 0.2792(3) 0.0401(5) Uani 1 1 d . . . . .
H8A H 0.571779 0.499490 0.374948 0.048 Uiso 1 1 calc R U . . .
C9A C 0.4084(4) 0.51919(6) 0.1831(3) 0.0384(5) Uani 1 1 d . . . . .
H9A H 0.438392 0.541023 0.211953 0.046 Uiso 1 1 calc R U . . .
C10A C 0.2819(4) 0.51203(6) 0.0402(3) 0.0361(5) Uani 1 1 d . . . . .
C11A C -0.1022(4) 0.55853(6) -0.4301(3) 0.0391(5) Uani 1 1 d . . . . .
C12A C 0.0935(4) 0.64220(6) -0.1922(3) 0.0368(5) Uani 1 1 d . . . . .
C13A C 0.0471(4) 0.66878(6) -0.2862(3) 0.0386(5) Uani 1 1 d . . . . .
H13A H -0.019443 0.665234 -0.387366 0.046 Uiso 1 1 calc R U . . .
C14A C 0.0942(4) 0.70015(6) -0.2381(3) 0.0384(5) Uani 1 1 d . . . . .
H14A H 0.063047 0.717742 -0.305110 0.046 Uiso 1 1 calc R U . . .
C15A C 0.1883(4) 0.70542(6) -0.0889(3) 0.0369(5) Uani 1 1 d . . . . .
C16A C 0.2317(4) 0.67927(6) 0.0068(3) 0.0387(5) Uani 1 1 d . . . . .
H16A H 0.294316 0.683059 0.108257 0.046 Uiso 1 1 calc R U . . .
C17A C 0.1867(4) 0.64805(6) -0.0411(3) 0.0381(5) Uani 1 1 d . . . . .
H17A H 0.217808 0.630562 0.026534 0.046 Uiso 1 1 calc R U . . .
C18A C 0.1878(4) 0.76351(6) -0.1113(3) 0.0404(5) Uani 1 1 d . . . . .
H18C H 0.044803 0.764207 -0.165021 0.049 Uiso 1 1 calc R U . . .
H18D H 0.257605 0.764631 -0.182548 0.049 Uiso 1 1 calc R U . . .
C19A C 0.2467(4) 0.79122(6) -0.0037(3) 0.0399(5) Uani 1 1 d . . . . .
H19C H 0.180709 0.788796 0.069499 0.048 Uiso 1 1 calc R U . . .
H19D H 0.389947 0.789881 0.048649 0.048 Uiso 1 1 calc R U . . .
C20A C 0.1958(4) 0.82420(6) -0.0743(3) 0.0395(5) Uani 1 1 d . . . . .
H20C H 0.051526 0.826399 -0.118737 0.047 Uiso 1 1 calc R U . . .
H20D H 0.251967 0.825990 -0.153475 0.047 Uiso 1 1 calc R U . . .
C21A C 0.2730(4) 0.85180(6) 0.0345(3) 0.0421(6) Uani 1 1 d . . . . .
H21C H 0.418054 0.851518 0.066525 0.050 Uiso 1 1 calc R U . . .
H21D H 0.226308 0.872635 -0.016441 0.050 Uiso 1 1 calc R U . . .
C22A C 0.2116(4) 0.85042(7) 0.1694(3) 0.0433(6) Uani 1 1 d . . . . .
H22C H 0.067338 0.848319 0.138099 0.052 Uiso 1 1 calc R U . . .
H22D H 0.271551 0.830954 0.227440 0.052 Uiso 1 1 calc R U . . .
C23A C 0.2724(5) 0.88025(7) 0.2650(3) 0.0491(7) Uani 1 1 d . . . . .
H23D H 0.202094 0.899317 0.211565 0.074 Uiso 1 1 calc R U . . .
H23E H 0.413957 0.883291 0.290851 0.074 Uiso 1 1 calc R U . . .
H23F H 0.240322 0.877381 0.354117 0.074 Uiso 1 1 calc R U . . .
C24A C 0.4879(4) 0.40636(6) 0.3134(3) 0.0406(5) Uani 1 1 d . . . . .
H24C H 0.519284 0.399583 0.226146 0.049 Uiso 1 1 calc R U . . .
H24D H 0.345735 0.403408 0.292615 0.049 Uiso 1 1 calc R U . . .
C25A C 0.6044(4) 0.38587(7) 0.4437(3) 0.0435(6) Uani 1 1 d . . . . .
C26A C 0.5436(4) 0.35044(7) 0.4166(3) 0.0441(6) Uani 1 1 d . . . . .
H26C H 0.403494 0.348798 0.406603 0.053 Uiso 1 1 calc R U . . .
H26D H 0.556948 0.343463 0.323122 0.053 Uiso 1 1 calc R U . . .
C27A C 0.6638(4) 0.32738(7) 0.5375(3) 0.0450(6) Uani 1 1 d . . . . .
H27C H 0.802924 0.328081 0.544023 0.054 Uiso 1 1 calc R U . . .
H27D H 0.656106 0.334962 0.631943 0.054 Uiso 1 1 calc R U . . .
C28A C 0.5950(6) 0.29260(8) 0.5131(4) 0.0605(8) Uani 1 1 d . . . . .
H28C H 0.593689 0.285539 0.415532 0.073 Uiso 1 1 calc R U . . .
H28D H 0.458892 0.291672 0.513552 0.073 Uiso 1 1 calc R U . . .
C29A C 0.7232(7) 0.26918(8) 0.6278(4) 0.0720(11) Uani 1 1 d . . . . .
H29D H 0.673462 0.247160 0.604890 0.108 Uiso 1 1 calc R U . . .
H29E H 0.720322 0.275384 0.724223 0.108 Uiso 1 1 calc R U . . .
H29F H 0.858362 0.269928 0.628015 0.108 Uiso 1 1 calc R U . . .
B1A B 0.2113(4) 0.57347(7) -0.0334(3) 0.0361(6) 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 1.360(3) . ?
F2 B1 1.364(3) . ?
O1 C15 1.352(3) . ?
O1 C18 1.441(3) . ?
O2 C7 1.367(3) . ?
O2 C24 1.428(3) . ?
N1 N2 1.300(3) . ?
N1 C1 1.349(3) . ?
N1 B1 1.652(3) . ?
N2 C12 1.391(3) . ?
N3 C2 1.349(3) . ?
N3 C10 1.388(3) . ?
N3 B1 1.567(4) . ?
N4 C11 1.157(3) . ?
C1 C2 1.419(3) . ?
C1 C11 1.412(3) . ?
C2 C3 1.396(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.363(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.431(4) . ?
C5 C6 1.411(3) . ?
C5 C10 1.407(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.379(4) . ?
C7 C8 1.400(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.377(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.409(4) . ?
C12 C13 1.411(3) . ?
C12 C17 1.404(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.368(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.394(4) . ?
C15 C16 1.402(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.391(4) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.511(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.520(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.526(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.528(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.518(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.514(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.516(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.519(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.535(5) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.514(4) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
F1A B1A 1.376(3) . ?
F2A B1A 1.361(3) . ?
O1A C15A 1.356(3) . ?
O1A C18A 1.428(3) . ?
O2A C7A 1.358(3) . ?
O2A C24A 1.434(3) . ?
N1A N2A 1.289(3) . ?
N1A C1A 1.368(3) . ?
N1A B1A 1.644(4) . ?
N2A C12A 1.399(3) . ?
N3A C2A 1.355(3) . ?
N3A C10A 1.374(4) . ?
N3A B1A 1.561(3) . ?
N4A C11A 1.152(4) . ?
C1A C2A 1.413(4) . ?
C1A C11A 1.415(4) . ?
C2A C3A 1.408(3) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.354(4) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.432(3) . ?
C5A C6A 1.406(4) . ?
C5A C10A 1.412(3) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.384(4) . ?
C7A C8A 1.409(4) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.366(4) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.414(3) . ?
C12A C13A 1.393(4) . ?
C12A C17A 1.416(3) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.384(3) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.397(3) . ?
C15A C16A 1.389(4) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.376(3) . ?
C17A H17A 0.9500 . ?
C18A H18C 0.9900 . ?
C18A H18D 0.9900 . ?
C18A C19A 1.515(3) . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C19A C20A 1.510(4) . ?
C20A H20C 0.9900 . ?
C20A H20D 0.9900 . ?
C20A C21A 1.531(3) . ?
C21A H21C 0.9900 . ?
C21A H21D 0.9900 . ?
C21A C22A 1.525(4) . ?
C22A H22C 0.9900 . ?
C22A H22D 0.9900 . ?
C22A C23A 1.520(3) . ?
C23A H23D 0.9800 . ?
C23A H23E 0.9800 . ?
C23A H23F 0.9800 . ?
C24A H24C 0.9900 . ?
C24A H24D 0.9900 . ?
C24A C25A 1.515(4) . ?
C25A C26A 1.530(4) . ?
C26A H26C 0.9900 . ?
C26A H26D 0.9900 . ?
C26A C27A 1.528(4) . ?
C27A H27C 0.9900 . ?
C27A H27D 0.9900 . ?
C27A C28A 1.518(4) . ?
C28A H28C 0.9900 . ?
C28A H28D 0.9900 . ?
C28A C29A 1.523(5) . ?
C29A H29D 0.9800 . ?
C29A H29E 0.9800 . ?
C29A H29F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O1 C18 120.04(19) . . ?
C7 O2 C24 116.4(2) . . ?
N2 N1 C1 116.4(2) . . ?
N2 N1 B1 135.5(2) . . ?
C1 N1 B1 108.02(19) . . ?
N1 N2 C12 124.5(2) . . ?
C2 N3 C10 120.7(2) . . ?
C2 N3 B1 111.64(19) . . ?
C10 N3 B1 127.6(2) . . ?
N1 C1 C2 112.4(2) . . ?
N1 C1 C11 123.5(2) . . ?
C11 C1 C2 124.1(2) . . ?
N3 C2 C1 110.8(2) . . ?
N3 C2 C3 122.0(2) . . ?
C3 C2 C1 127.2(2) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.1(2) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.3(2) . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 121.1(2) . . ?
C10 C5 C4 118.8(2) . . ?
C10 C5 C6 120.1(2) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.5(2) . . ?
C7 C6 H6 120.3 . . ?
O2 C7 C6 124.3(2) . . ?
O2 C7 C8 115.7(2) . . ?
C6 C7 C8 120.0(2) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 C7 121.7(2) . . ?
C9 C8 H8 119.1 . . ?
C8 C9 H9 120.5 . . ?
C8 C9 C10 118.9(2) . . ?
C10 C9 H9 120.5 . . ?
N3 C10 C5 119.1(2) . . ?
N3 C10 C9 121.1(2) . . ?
C5 C10 C9 119.7(2) . . ?
N4 C11 C1 178.2(3) . . ?
N2 C12 C13 111.0(2) . . ?
N2 C12 C17 131.2(2) . . ?
C17 C12 C13 117.8(2) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 C12 121.6(2) . . ?
C14 C13 H13 119.2 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.5(2) . . ?
C15 C14 H14 119.8 . . ?
O1 C15 C14 115.2(2) . . ?
O1 C15 C16 125.6(2) . . ?
C14 C15 C16 119.2(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 H17 119.7 . . ?
C16 C17 C12 120.6(2) . . ?
C16 C17 H17 119.7 . . ?
O1 C18 H18A 110.4 . . ?
O1 C18 H18B 110.4 . . ?
O1 C18 C19 106.72(19) . . ?
H18A C18 H18B 108.6 . . ?
C19 C18 H18A 110.4 . . ?
C19 C18 H18B 110.4 . . ?
C18 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
C18 C19 C20 112.6(2) . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C19 C20 H20A 109.1 . . ?
C19 C20 H20B 109.1 . . ?
C19 C20 C21 112.7(2) . . ?
H20A C20 H20B 107.8 . . ?
C21 C20 H20A 109.1 . . ?
C21 C20 H20B 109.1 . . ?
C20 C21 H21A 108.8 . . ?
C20 C21 H21B 108.8 . . ?
C20 C21 C22 114.0(2) . . ?
H21A C21 H21B 107.6 . . ?
C22 C21 H21A 108.8 . . ?
C22 C21 H21B 108.8 . . ?
C21 C22 H22A 108.9 . . ?
C21 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C23 C22 C21 113.5(2) . . ?
C23 C22 H22A 108.9 . . ?
C23 C22 H22B 108.9 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O2 C24 H24A 109.6 . . ?
O2 C24 H24B 109.6 . . ?
O2 C24 C25 110.2(2) . . ?
H24A C24 H24B 108.1 . . ?
C25 C24 H24A 109.6 . . ?
C25 C24 H24B 109.6 . . ?
C24 C25 H25A 109.9 . . ?
C24 C25 H25B 109.9 . . ?
C24 C25 C26 108.9(2) . . ?
H25A C25 H25B 108.3 . . ?
C26 C25 H25A 109.9 . . ?
C26 C25 H25B 109.9 . . ?
C25 C26 H26A 108.3 . . ?
C25 C26 H26B 108.3 . . ?
C25 C26 C27 115.9(2) . . ?
H26A C26 H26B 107.4 . . ?
C27 C26 H26A 108.3 . . ?
C27 C26 H26B 108.3 . . ?
C26 C27 H27A 109.2 . . ?
C26 C27 H27B 109.2 . . ?
C26 C27 C28 112.0(3) . . ?
H27A C27 H27B 107.9 . . ?
C28 C27 H27A 109.2 . . ?
C28 C27 H27B 109.2 . . ?
C27 C28 H28A 108.9 . . ?
C27 C28 H28B 108.9 . . ?
H28A C28 H28B 107.7 . . ?
C29 C28 C27 113.4(3) . . ?
C29 C28 H28A 108.9 . . ?
C29 C28 H28B 108.9 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
F1 B1 F2 113.8(2) . . ?
F1 B1 N1 109.96(19) . . ?
F1 B1 N3 112.5(2) . . ?
F2 B1 N1 110.58(19) . . ?
F2 B1 N3 111.7(2) . . ?
N3 B1 N1 97.10(19) . . ?
C15A O1A C18A 119.9(2) . . ?
C7A O2A C24A 117.4(2) . . ?
N2A N1A C1A 117.9(2) . . ?
N2A N1A B1A 134.75(19) . . ?
C1A N1A B1A 107.4(2) . . ?
N1A N2A C12A 122.5(2) . . ?
C2A N3A C10A 121.6(2) . . ?
C2A N3A B1A 110.8(2) . . ?
C10A N3A B1A 127.5(2) . . ?
N1A C1A C2A 112.0(2) . . ?
N1A C1A C11A 123.4(2) . . ?
C2A C1A C11A 124.5(2) . . ?
N3A C2A C1A 111.5(2) . . ?
N3A C2A C3A 120.8(2) . . ?
C3A C2A C1A 127.8(2) . . ?
C2A C3A H3A 120.5 . . ?
C4A C3A C2A 119.1(2) . . ?
C4A C3A H3A 120.5 . . ?
C3A C4A H4A 119.4 . . ?
C3A C4A C5A 121.2(2) . . ?
C5A C4A H4A 119.4 . . ?
C6A C5A C4A 121.8(2) . . ?
C6A C5A C10A 120.3(2) . . ?
C10A C5A C4A 117.9(2) . . ?
C5A C6A H6A 120.1 . . ?
C7A C6A C5A 119.7(2) . . ?
C7A C6A H6A 120.1 . . ?
O2A C7A C6A 124.8(2) . . ?
O2A C7A C8A 115.7(2) . . ?
C6A C7A C8A 119.5(3) . . ?
C7A C8A H8A 119.1 . . ?
C9A C8A C7A 121.7(2) . . ?
C9A C8A H8A 119.1 . . ?
C8A C9A H9A 120.2 . . ?
C8A C9A C10A 119.6(2) . . ?
C10A C9A H9A 120.2 . . ?
N3A C10A C5A 119.5(2) . . ?
N3A C10A C9A 121.4(2) . . ?
C5A C10A C9A 119.1(2) . . ?
N4A C11A C1A 176.8(3) . . ?
N2A C12A C17A 129.2(2) . . ?
C13A C12A N2A 112.9(2) . . ?
C13A C12A C17A 117.9(2) . . ?
C12A C13A H13A 118.7 . . ?
C14A C13A C12A 122.6(2) . . ?
C14A C13A H13A 118.7 . . ?
C13A C14A H14A 120.7 . . ?
C13A C14A C15A 118.7(2) . . ?
C15A C14A H14A 120.7 . . ?
O1A C15A C14A 125.5(2) . . ?
O1A C15A C16A 115.0(2) . . ?
C16A C15A C14A 119.5(2) . . ?
C15A C16A H16A 119.1 . . ?
C17A C16A C15A 121.9(2) . . ?
C17A C16A H16A 119.1 . . ?
C12A C17A H17A 120.3 . . ?
C16A C17A C12A 119.4(2) . . ?
C16A C17A H17A 120.3 . . ?
O1A C18A H18C 110.6 . . ?
O1A C18A H18D 110.6 . . ?
O1A C18A C19A 105.6(2) . . ?
H18C C18A H18D 108.7 . . ?
C19A C18A H18C 110.6 . . ?
C19A C18A H18D 110.6 . . ?
C18A C19A H19C 108.9 . . ?
C18A C19A H19D 108.9 . . ?
H19C C19A H19D 107.7 . . ?
C20A C19A C18A 113.5(2) . . ?
C20A C19A H19C 108.9 . . ?
C20A C19A H19D 108.9 . . ?
C19A C20A H20C 109.1 . . ?
C19A C20A H20D 109.1 . . ?
C19A C20A C21A 112.5(2) . . ?
H20C C20A H20D 107.8 . . ?
C21A C20A H20C 109.1 . . ?
C21A C20A H20D 109.1 . . ?
C20A C21A H21C 108.6 . . ?
C20A C21A H21D 108.6 . . ?
H21C C21A H21D 107.6 . . ?
C22A C21A C20A 114.7(2) . . ?
C22A C21A H21C 108.6 . . ?
C22A C21A H21D 108.6 . . ?
C21A C22A H22C 109.1 . . ?
C21A C22A H22D 109.1 . . ?
H22C C22A H22D 107.8 . . ?
C23A C22A C21A 112.6(2) . . ?
C23A C22A H22C 109.1 . . ?
C23A C22A H22D 109.1 . . ?
C22A C23A H23D 109.5 . . ?
C22A C23A H23E 109.5 . . ?
C22A C23A H23F 109.5 . . ?
H23D C23A H23E 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
O2A C24A H24C 109.9 . . ?
O2A C24A H24D 109.9 . . ?
O2A C24A C25A 109.0(2) . . ?
H24C C24A H24D 108.3 . . ?
C25A C24A H24C 109.9 . . ?
C25A C24A H24D 109.9 . . ?
C24A C25A C26A 109.9(2) . . ?
C25A C26A H26C 108.8 . . ?
C25A C26A H26D 108.8 . . ?
H26C C26A H26D 107.7 . . ?
C27A C26A C25A 113.8(2) . . ?
C27A C26A H26C 108.8 . . ?
C27A C26A H26D 108.8 . . ?
C26A C27A H27C 108.9 . . ?
C26A C27A H27D 108.9 . . ?
H27C C27A H27D 107.7 . . ?
C28A C27A C26A 113.2(2) . . ?
C28A C27A H27C 108.9 . . ?
C28A C27A H27D 108.9 . . ?
C27A C28A H28C 108.9 . . ?
C27A C28A H28D 108.9 . . ?
C27A C28A C29A 113.3(3) . . ?
H28C C28A H28D 107.7 . . ?
C29A C28A H28C 108.9 . . ?
C29A C28A H28D 108.9 . . ?
C28A C29A H29D 109.5 . . ?
C28A C29A H29E 109.5 . . ?
C28A C29A H29F 109.5 . . ?
H29D C29A H29E 109.5 . . ?
H29D C29A H29F 109.5 . . ?
H29E C29A H29F 109.5 . . ?
F1A B1A N1A 110.1(2) . . ?
F1A B1A N3A 110.2(2) . . ?
F2A B1A F1A 113.0(2) . . ?
F2A B1A N1A 111.5(2) . . ?
F2A B1A N3A 113.0(2) . . ?
N3A B1A N1A 98.16(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
O1 C15 C16 C17 179.9(2) . . . . ?
O1 C18 C19 C20 -178.1(2) . . . . ?
O2 C7 C8 C9 -179.4(2) . . . . ?
O2 C24 C25 C26 -177.5(2) . . . . ?
N1 N2 C12 C13 -175.9(2) . . . . ?
N1 N2 C12 C17 4.9(4) . . . . ?
N1 C1 C2 N3 0.8(3) . . . . ?
N1 C1 C2 C3 179.8(2) . . . . ?
N2 N1 C1 C2 -178.9(2) . . . . ?
N2 N1 C1 C11 -0.8(3) . . . . ?
N2 N1 B1 F1 60.9(3) . . . . ?
N2 N1 B1 F2 -65.6(3) . . . . ?
N2 N1 B1 N3 178.0(2) . . . . ?
N2 C12 C13 C14 -179.6(2) . . . . ?
N2 C12 C17 C16 179.0(2) . . . . ?
N3 C2 C3 C4 0.0(4) . . . . ?
C1 N1 N2 C12 178.8(2) . . . . ?
C1 N1 B1 F1 -118.1(2) . . . . ?
C1 N1 B1 F2 115.4(2) . . . . ?
C1 N1 B1 N3 -1.0(2) . . . . ?
C1 C2 C3 C4 -178.9(2) . . . . ?
C2 N3 C10 C5 0.0(3) . . . . ?
C2 N3 C10 C9 -179.0(2) . . . . ?
C2 N3 B1 F1 116.6(2) . . . . ?
C2 N3 B1 F2 -114.0(2) . . . . ?
C2 N3 B1 N1 1.5(2) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 179.8(2) . . . . ?
C3 C4 C5 C10 -0.2(4) . . . . ?
C4 C5 C6 C7 -179.8(2) . . . . ?
C4 C5 C10 N3 0.2(3) . . . . ?
C4 C5 C10 C9 179.1(2) . . . . ?
C5 C6 C7 O2 179.7(2) . . . . ?
C5 C6 C7 C8 0.1(4) . . . . ?
C6 C5 C10 N3 -179.9(2) . . . . ?
C6 C5 C10 C9 -0.9(3) . . . . ?
C6 C7 C8 C9 0.3(4) . . . . ?
C7 O2 C24 C25 178.6(2) . . . . ?
C7 C8 C9 C10 -0.9(4) . . . . ?
C8 C9 C10 N3 -179.8(2) . . . . ?
C8 C9 C10 C5 1.2(3) . . . . ?
C10 N3 C2 C1 179.0(2) . . . . ?
C10 N3 C2 C3 0.0(3) . . . . ?
C10 N3 B1 F1 -64.0(3) . . . . ?
C10 N3 B1 F2 65.4(3) . . . . ?
C10 N3 B1 N1 -179.1(2) . . . . ?
C10 C5 C6 C7 0.3(3) . . . . ?
C11 C1 C2 N3 -177.4(2) . . . . ?
C11 C1 C2 C3 1.6(4) . . . . ?
C12 C13 C14 C15 0.5(4) . . . . ?
C13 C12 C17 C16 -0.2(4) . . . . ?
C13 C14 C15 O1 179.6(2) . . . . ?
C13 C14 C15 C16 -0.2(4) . . . . ?
C14 C15 C16 C17 -0.3(4) . . . . ?
C15 O1 C18 C19 173.2(2) . . . . ?
C15 C16 C17 C12 0.5(4) . . . . ?
C17 C12 C13 C14 -0.3(4) . . . . ?
C18 O1 C15 C14 -174.1(2) . . . . ?
C18 O1 C15 C16 5.7(4) . . . . ?
C18 C19 C20 C21 179.1(2) . . . . ?
C19 C20 C21 C22 177.8(2) . . . . ?
C20 C21 C22 C23 62.7(3) . . . . ?
C24 O2 C7 C6 3.2(3) . . . . ?
C24 O2 C7 C8 -177.2(2) . . . . ?
C24 C25 C26 C27 -177.0(2) . . . . ?
C25 C26 C27 C28 178.1(2) . . . . ?
C26 C27 C28 C29 -175.5(3) . . . . ?
B1 N1 N2 C12 -0.2(4) . . . . ?
B1 N1 C1 C2 0.3(3) . . . . ?
B1 N1 C1 C11 178.5(2) . . . . ?
B1 N3 C2 C1 -1.5(3) . . . . ?
B1 N3 C2 C3 179.4(2) . . . . ?
B1 N3 C10 C5 -179.4(2) . . . . ?
B1 N3 C10 C9 1.7(4) . . . . ?
O1A C15A C16A C17A -179.9(2) . . . . ?
O1A C18A C19A C20A -178.5(2) . . . . ?
O2A C7A C8A C9A 178.7(2) . . . . ?
O2A C24A C25A C26A 175.9(2) . . . . ?
N1A N2A C12A C13A 172.0(2) . . . . ?
N1A N2A C12A C17A -9.7(4) . . . . ?
N1A C1A C2A N3A -1.2(3) . . . . ?
N1A C1A C2A C3A 178.9(2) . . . . ?
N2A N1A C1A C2A 178.6(2) . . . . ?
N2A N1A C1A C11A -0.5(4) . . . . ?
N2A N1A B1A F1A 68.0(3) . . . . ?
N2A N1A B1A F2A -58.3(3) . . . . ?
N2A N1A B1A N3A -177.0(2) . . . . ?
N2A C12A C13A C14A -179.4(2) . . . . ?
N2A C12A C17A C16A -179.6(2) . . . . ?
N3A C2A C3A C4A 1.2(3) . . . . ?
C1A N1A N2A C12A -179.9(2) . . . . ?
C1A N1A B1A F1A -111.7(2) . . . . ?
C1A N1A B1A F2A 122.1(2) . . . . ?
C1A N1A B1A N3A 3.4(2) . . . . ?
C1A C2A C3A C4A -178.9(2) . . . . ?
C2A N3A C10A C5A -1.4(3) . . . . ?
C2A N3A C10A C9A 177.9(2) . . . . ?
C2A N3A B1A F1A 110.8(2) . . . . ?
C2A N3A B1A F2A -121.8(2) . . . . ?
C2A N3A B1A N1A -4.2(2) . . . . ?
C2A C3A C4A C5A -0.9(4) . . . . ?
C3A C4A C5A C6A -179.6(2) . . . . ?
C3A C4A C5A C10A -0.5(3) . . . . ?
C4A C5A C6A C7A 177.3(2) . . . . ?
C4A C5A C10A N3A 1.6(3) . . . . ?
C4A C5A C10A C9A -177.6(2) . . . . ?
C5A C6A C7A O2A -177.8(2) . . . . ?
C5A C6A C7A C8A 1.1(4) . . . . ?
C6A C5A C10A N3A -179.2(2) . . . . ?
C6A C5A C10A C9A 1.5(3) . . . . ?
C6A C7A C8A C9A -0.3(4) . . . . ?
C7A O2A C24A C25A -180.0(2) . . . . ?
C7A C8A C9A C10A 0.0(4) . . . . ?
C8A C9A C10A N3A -179.9(2) . . . . ?
C8A C9A C10A C5A -0.7(3) . . . . ?
C10A N3A C2A C1A -180.0(2) . . . . ?
C10A N3A C2A C3A -0.1(3) . . . . ?
C10A N3A B1A F1A -65.3(3) . . . . ?
C10A N3A B1A F2A 62.2(3) . . . . ?
C10A N3A B1A N1A 179.8(2) . . . . ?
C10A C5A C6A C7A -1.8(3) . . . . ?
C11A C1A C2A N3A 177.9(2) . . . . ?
C11A C1A C2A C3A -2.0(4) . . . . ?
C12A C13A C14A C15A -1.4(4) . . . . ?
C13A C12A C17A C16A -1.5(4) . . . . ?
C13A C14A C15A O1A -179.4(2) . . . . ?
C13A C14A C15A C16A -0.1(4) . . . . ?
C14A C15A C16A C17A 0.8(4) . . . . ?
C15A O1A C18A C19A 172.7(2) . . . . ?
C15A C16A C17A C12A 0.1(4) . . . . ?
C17A C12A C13A C14A 2.1(4) . . . . ?
C18A O1A C15A C14A 5.3(4) . . . . ?
C18A O1A C15A C16A -174.0(2) . . . . ?
C18A C19A C20A C21A -174.9(2) . . . . ?
C19A C20A C21A C22A -54.0(3) . . . . ?
C20A C21A C22A C23A -173.5(2) . . . . ?
C24A O2A C7A C6A -5.4(4) . . . . ?
C24A O2A C7A C8A 175.6(2) . . . . ?
C24A C25A C26A C27A 175.7(2) . . . . ?
C25A C26A C27A C28A 177.0(3) . . . . ?
C26A C27A C28A C29A 176.0(3) . . . . ?
B1A N1A N2A C12A 0.5(4) . . . . ?
B1A N1A C1A C2A -1.6(3) . . . . ?
B1A N1A C1A C11A 179.2(2) . . . . ?
B1A N3A C2A C1A 3.7(3) . . . . ?
B1A N3A C2A C3A -176.4(2) . . . . ?
B1A N3A C10A C5A 174.3(2) . . . . ?
B1A N3A C10A C9A -6.4(4) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id AzoBF2-di6C
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.840
_oxdiff_exptl_absorpt_empirical_full_min 0.449
####################################################################### 
# 
# 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_ia423d
_database_code_depnum_ccdc_archive 'CCDC 2257909'
loop_
_audit_author_name
_audit_author_address
'Qingkai Qi'
;Dartmouth College
United States of America
;
_audit_update_record             
;
2023-04-20 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;
_audit_creation_date             2023-04-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H35 B F2 N4 O'
_chemical_formula_sum            'C29 H35 B F2 N4 O'
_chemical_formula_weight         504.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         C29H35BF2N4O
_chemical_oxdiff_usercomment     AzoBF2-12C
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'
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      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                   7.9249(2)
_cell_length_b                   11.3974(3)
_cell_length_c                   16.0639(4)
_cell_angle_alpha                98.410(2)
_cell_angle_beta                 102.690(2)
_cell_angle_gamma                108.100(2)
_cell_volume                     1308.96(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15549
_cell_measurement_temperature    100.0(4)
_cell_measurement_theta_max      78.9300
_cell_measurement_theta_min      2.8790
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.797
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.663
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0061
0 1 0 0.0317
0 0 -1 0.0077
0 0 1 0.0077
-1 0 0 0.1602
1 0 0 0.1354
-4 6 1 0.1552
0 1 -1 0.0252
0 -1 1 0.0064

_exptl_crystal_recrystallization_method 'used as recieved'
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.038
_exptl_crystal_size_min          0.015
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0004 -0.9993 0.0003 0.0179 -0.1076 0.0971
-0.0004 0.9993 -0.0003 -0.0179 0.1076 -0.0971
0.0010 -0.0005 -1.0018 -0.0947 -0.0298 0.0197
-0.0010 0.0005 1.0018 0.0947 0.0298 -0.0197
-1.0030 0.0006 -0.0016 -0.0445 0.0682 0.1977
1.0030 -0.0006 0.0016 0.0445 -0.0682 -0.1977
-4.3176 5.7873 1.2244 -0.1788 0.9526 0.2638
0.0006 0.9988 -1.0021 -0.1126 0.0778 -0.0775
-0.0006 -0.9988 1.0021 0.1126 -0.0778 0.0775

_exptl_special_details           
;
Data was collected using a Rigaku Synergy S Diffractometer diffractometer equipped 
with an Oxford 800 low-temperature apparatus.  A suitable 
crystal was chosen and mounted on a nylon loop using Paratone oil.  Data  were 
measured based on the Pre-Experiment plugin of CrysAlisPro software.  Cell 
parameters were retrieved using CrysAlisPro software and data reduction was 
performed using the intergration software inside the CrysAlisPro which 
corrects for Lp.  The structure was solved by the direct method using the 
SHELXT program and refined by least squares method on F2, SHELXL,
 incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            43444
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.287
_diffrn_reflns_theta_min         2.898
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  10.00   0.50    2.24    --   10.00  84.00 163.38   52
  2  ω     -7.00  19.00   0.50    2.24    --   14.00  74.00-120.83   52
  3  ω      0.00  26.00   0.50    2.24    --   18.00  66.00 138.19   52
  4  ω      7.00  37.00   0.50    2.24    --   22.00  58.00 -71.02   60
  5  ω      5.00  31.00   0.50    2.24    --   22.00  62.00-123.04   52
  6  ω     12.00  42.00   0.50    2.24    --   26.00  55.00  10.62   60
  7  ω     11.00  37.00   0.50    2.24    --   26.00  58.00 -27.66   52
  8  ω     16.00  44.00   0.50    2.24    --   30.00  54.00 -91.40   56
  9  ω     16.00  42.00   0.50    2.24    --   30.00  55.00 -16.21   52
 10  ω     16.00  42.00   0.50    2.24    --   30.00  55.00 120.43   52
 11  ω     20.00  46.00   0.50    2.24    --   34.00  53.00  61.36   52
 12  ω     20.00  48.00   0.50    2.24    --   34.00  52.00  91.00   56
 13  ω     24.00  50.00   0.50    2.24    --   38.00  51.00 175.31   52
 14  ω     25.00  53.00   0.50    2.24    --   38.00  50.00 157.61   56
 15  ω    -80.00  -4.00   0.50    2.24    --  -46.85 111.00  64.00  152
 16  ω     26.00  84.00   0.50    2.24    --   46.85-111.00 -29.00  116
 17  ω   -118.00 -34.00   0.50    2.24    --  -46.85 -45.00-157.47  168
 18  ω    -82.00 -15.00   0.50    2.24    --  -46.85 125.00-180.00  134
 19  ω     36.00  93.00   0.50    2.24    --   46.85-125.00-120.00  114
 20  ω     36.00  93.00   0.50    2.24    --   46.85-125.00 -60.00  114
 21  ω   -121.00 -37.00   0.50    2.24    --  -50.00 -46.00  18.51  168
 22  ω   -122.00 -37.00   0.50    2.24    --  -50.00 -45.00 103.58  170
 23  ω   -130.00 -45.00   0.50    2.24    --  -58.00 -42.00  64.91  170
 24  ω   -134.00 -49.00   0.50    2.24    --  -62.00 -47.00 177.67  170
 25  ω   -138.00 -53.00   0.50    2.24    --  -66.00 -47.00 -64.90  170
 26  ω   -138.00 -53.00   0.50    2.24    --  -66.00 -47.00  -0.74  170
 27  ω   -138.00 -52.00   0.50    2.24    --  -66.00 -44.00-157.69  172
 28  ω   -138.00 -53.00   0.50    2.24    --  -66.00 -45.00 -43.00  170
 29  ω   -142.00 -57.00   0.50    2.24    --  -70.00 -46.00  41.46  170
 30  ω   -142.00 -57.00   0.50    2.24    --  -70.00 -47.00-101.90  170
 31  ω   -142.00 -57.00   0.50    2.24    --  -70.00 -47.00 -16.68  170
 32  ω   -142.00 -57.00   0.50    2.24    --  -70.00 -47.00  28.39  170
 33  ω   -142.00 -57.00   0.50    2.24    --  -70.00 -47.00 164.05  170
 34  ω   -142.00 -57.00   0.50    2.24    --  -70.00 -46.00 115.42  170
 35  ω   -146.00 -61.00   0.50    2.24    --  -74.00 -45.00  74.34  170
 36  ω   -146.00 -60.00   0.50    2.24    --  -74.00 -44.00  97.44  172
 37  ω   -146.00 -61.00   0.50    2.24    --  -74.00 -45.00 -80.64  170
 38  ω   -145.00 -61.00   0.50    2.24    --  -74.00 -46.00 -50.04  168
 39  ω   -146.00 -61.00   0.50    2.24    --  -74.00 -45.00-113.88  170
 40  ω    -95.00 -62.00   0.50    2.24    --  -74.00 -41.00 132.81   66
 41  ω    -94.00 -69.00   0.50    8.95    --  -82.00 -46.00  49.22   50
 42  ω    -96.00 -69.00   0.50    8.95    --  -82.00 -46.00-135.39   54
 43  ω    -95.00 -69.00   0.50    8.95    --  -82.00 -45.00-167.58   52
 44  ω   -160.00 -83.00   0.50    8.95    --  -91.75-111.00 -29.00  154
 45  ω    -80.00 -23.00   0.50    8.95    --  -91.75 111.00  64.00  114
 46  ω   -116.00 -79.00   0.50    8.95    --  -91.75 -46.00 145.34   74
 47  ω   -163.00-132.00   0.50    8.95    --  -91.75 -45.00 120.00   62
 48  ω   -162.00-110.00   0.50    8.95    --  -91.75 -45.00 -90.00  104
 49  ω   -124.00 -80.00   0.50    8.95    --  -91.75 -46.00  79.33   88
 50  ω   -107.00 -81.00   0.50    8.95    --  -91.75 -45.00-146.14   52
 51  ω   -104.00 -79.00   0.50    8.95    --  -91.75 -45.00  46.21   50
 52  ω   -152.00-127.00   0.50    8.95    --  -91.75 -45.00  46.21   50
 53  ω   -105.00 -79.00   0.50    8.95    --  -91.75 -46.00-112.72   52
 54  ω   -112.00 -80.00   0.50    8.95    --  -91.75 -45.00 -30.00   64
 55  ω   -114.00 -79.00   0.50    8.95    --  -91.75 -46.00 173.35   70
 56  ω   -147.00-120.00   0.50    8.95    --  -91.75 -46.00 173.35   54
 57  ω   -111.00 -82.00   0.50    8.95    --  -91.75 -45.00 -47.59   58
 58  ω   -108.00 -82.00   0.50    8.95    --  -91.75 -47.00 -69.58   52
 59  ω   -107.00 -79.00   0.50    8.95    --  -91.75 -45.00   0.00   56
 60  ω   -104.00 -79.00   0.50    8.95    --  -91.75 -45.00 120.00   50
 61  ω   -163.00-127.00   0.50    8.95    --  -91.75 -45.00   0.00   72
 62  ω   -121.00 -84.00   0.50    8.95    --  -91.75 -47.00 109.49   74
 63  ω   -106.00 -79.00   0.50    8.95    --  -91.75 -45.00  30.00   54
 64  ω   -129.00 -86.00   0.50    8.95    --  -91.75 -47.00-163.54   86
 65  ω   -111.00 -79.00   0.50    8.95    --  -91.75 -46.00 -10.77   64
 66  ω   -105.00 -79.00   0.50    8.95    --  -91.75 -45.00 -90.00   52
 67  ω   -110.00 -83.00   0.50    8.95    --  -91.75 -47.00  20.27   54
 68  ω    105.00 178.00   0.50    8.95    --  113.25 111.00  64.00  146
 69  ω     45.00 106.00   0.50    8.95    --  113.25-111.00 -29.00  122
 70  ω    108.00 157.00   0.50    8.95    --  113.25 125.00 -60.00   98
 71  ω     53.00 107.00   0.50    8.95    --  113.25-125.00 -60.00  108
 72  ω    150.00 176.00   0.50    8.95    --  113.25  45.00-150.00   52
 73  ω    102.00 138.00   0.50    8.95    --  113.25  45.00-120.00   72
 74  ω    111.00 178.00   0.50    8.95    --  113.25  77.00   0.00  134
 75  ω    104.00 146.00   0.50    8.95    --  113.25  45.00-150.00   84
 76  ω    150.00 177.00   0.50    8.95    --  113.25  61.00 -90.00   54
 77  ω    107.00 136.00   0.50    8.95    --  113.25  61.00 -90.00   58
 78  ω    101.00 127.00   0.50    8.95    --  113.25  45.00-180.00   52
 79  ω     83.00 108.00   0.50    8.95    --  113.25-125.00  90.00   50
 80  ω     76.00 105.00   0.50    8.95    --  113.25-105.00 120.40   58
 81  ω    138.00 177.00   0.50    8.95    --  113.25  45.00  90.00   78
 82  ω     42.00  80.00   0.50    8.95    --  113.25 -77.00-150.00   76
 83  ω    148.00 178.00   0.50    8.95    --  113.25  61.00-180.00   60
 84  ω    101.00 136.00   0.50    8.95    --  113.25  45.00  90.00   70
 85  ω    107.00 144.00   0.50    8.95    --  113.25  61.00-180.00   74
 86  ω     44.00  89.00   0.50    8.95    --  113.25 -77.00-120.00   90
 87  ω     45.00 103.00   0.50    8.95    --  113.25-125.00 120.00  116
 88  ω     78.00 103.00   0.50    8.95    --  113.25 -94.00-180.00   50
 89  ω     54.00  79.00   0.50    8.95    --  113.25-125.00  90.00   50
 90  ω    101.00 159.00   0.50    8.95    --  113.25  45.00 120.00  116
 91  ω     79.00 104.00   0.50    8.95    --  113.25 -94.00 150.00   50
 92  ω     43.00  68.00   0.50    8.95    --  113.25 -94.00 150.00   50
 93  ω     76.00 102.00   0.50    8.95    --  113.25 -94.00-150.00   52
 94  ω     44.00  89.00   0.50    8.95    --  113.25 -77.00   0.00   90
 95  ω    108.00 171.00   0.50    8.95    --  113.25  61.00 -30.00  126
 96  ω     42.00  68.00   0.50    8.95    --  113.25 -94.00-150.00   52
 97  ω    102.00 129.00   0.50    8.95    --  113.25  45.00 -30.00   54
 98  ω     79.00 104.00   0.50    8.95    --  113.25 -94.00 120.00   50
 99  ω     42.00  74.00   0.50    8.95    --  113.25 -94.00-180.00   64
100  ω    109.00 159.00   0.50    8.95    --  113.25  45.00 -60.00  100
101  ω    106.00 176.00   0.50    8.95    --  113.25  61.00-120.00  140
102  ω     42.00  67.00   0.50    8.95    --  113.25 -77.00  60.00   50
103  ω    134.00 160.00   0.50    8.95    --  113.25  45.00 -90.00   52
104  ω    101.00 128.00   0.50    8.95    --  113.25  45.00 -90.00   54
105  ω     42.00  67.00   0.50    8.95    --  113.25 -94.00 120.00   50
106  ω    148.00 178.00   0.50    8.95    --  113.25  77.00 150.00   60
107  ω    116.00 129.00   0.50    8.95    --  113.25  77.00 150.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0442449000
_diffrn_orient_matrix_UB_12      -0.0178949000
_diffrn_orient_matrix_UB_13      0.0945681000
_diffrn_orient_matrix_UB_21      -0.0680077000
_diffrn_orient_matrix_UB_22      0.1076110000
_diffrn_orient_matrix_UB_23      0.0295837000
_diffrn_orient_matrix_UB_31      -0.1971203000
_diffrn_orient_matrix_UB_32      -0.0972880000
_diffrn_orient_matrix_UB_33      -0.0197884000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4761
_reflns_number_total             5503
_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 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.595
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         5503
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0902
_refine_ls_restrained_S_all      1.118
_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)+(0.1070P)²+1.9777P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2406
_refine_ls_wR_factor_ref         0.2478
_refine_special_details          
;
The structure was refined by Least Squares SHELXL incorporated 
in Olex2 software program. All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which were found 
by difference Fourier methods and refined isotropically when data permits.
;
_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:
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,
 H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B),
 C27(H27A,H27B), C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C16(H16),
 C17(H17)
2.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C)
;
_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 1.5033(3) 0.73492(17) 0.75430(12) 0.0413(5) Uani 1 1 d . . . . .
F2 F 1.4772(3) 0.81655(17) 0.88743(12) 0.0408(5) Uani 1 1 d . . . . .
O1 O 0.6200(3) 0.50831(19) 0.67228(15) 0.0351(5) Uani 1 1 d . . . . .
N1 N 1.4661(4) 0.5946(3) 0.85922(19) 0.0438(7) Uani 1 1 d . . . . .
N2 N 1.3118(5) 0.5098(3) 0.84597(19) 0.0459(7) Uani 1 1 d . . . . .
N3 N 1.7489(4) 0.7648(2) 0.88194(16) 0.0330(6) Uani 1 1 d . . . . .
N4 N 1.6074(4) 0.3557(3) 0.9425(2) 0.0479(7) Uani 1 1 d . . . . .
C1 C 1.6163(4) 0.5644(3) 0.9004(2) 0.0353(7) Uani 1 1 d . . . . .
C2 C 1.7810(4) 0.6680(3) 0.91325(19) 0.0329(6) Uani 1 1 d . . . . .
C3 C 1.9642(5) 0.6771(3) 0.9537(2) 0.0373(7) Uani 1 1 d . . . . .
H3 H 1.986403 0.609175 0.976462 0.045 Uiso 1 1 calc R U . . .
C4 C 2.1061(5) 0.7830(3) 0.9593(2) 0.0380(7) Uani 1 1 d . . . . .
H4 H 2.229004 0.789117 0.985936 0.046 Uiso 1 1 calc R U . . .
C5 C 2.0752(4) 0.8866(3) 0.92604(19) 0.0362(7) Uani 1 1 d . . . . .
C6 C 2.2171(5) 0.9993(3) 0.9321(2) 0.0400(7) Uani 1 1 d . . . . .
H6 H 2.341494 1.008670 0.958737 0.048 Uiso 1 1 calc R U . . .
C7 C 2.1812(5) 1.0966(3) 0.9007(2) 0.0424(8) Uani 1 1 d . . . . .
H7 H 2.279462 1.173210 0.906005 0.051 Uiso 1 1 calc R U . . .
C8 C 1.9981(5) 1.0823(3) 0.8605(2) 0.0413(8) Uani 1 1 d . . . . .
H8 H 1.973472 1.149469 0.837654 0.050 Uiso 1 1 calc R U . . .
C9 C 1.8536(4) 0.9738(3) 0.8533(2) 0.0354(7) Uani 1 1 d . . . . .
H9 H 1.730149 0.965863 0.826185 0.043 Uiso 1 1 calc R U . . .
C10 C 1.8906(4) 0.8737(3) 0.88687(19) 0.0334(6) Uani 1 1 d . . . . .
C11 C 1.6099(4) 0.4487(3) 0.9243(2) 0.0378(7) Uani 1 1 d . . . . .
C12 C 1.1464(5) 0.5281(3) 0.8017(2) 0.0402(8) Uani 1 1 d . . . . .
C13 C 1.1161(4) 0.6248(3) 0.7611(2) 0.0394(7) Uani 1 1 d . . . . .
H13 H 1.218145 0.696771 0.762471 0.047 Uiso 1 1 calc R U . . .
C14 C 0.9381(4) 0.6144(3) 0.7195(2) 0.0350(7) Uani 1 1 d . . . . .
H14 H 0.918263 0.679727 0.692571 0.042 Uiso 1 1 calc R U . . .
C15 C 0.7880(4) 0.5090(3) 0.7166(2) 0.0325(6) Uani 1 1 d . . . . .
C16 C 0.8171(5) 0.4151(3) 0.7579(2) 0.0389(7) Uani 1 1 d . . . . .
H16 H 0.714835 0.343785 0.757386 0.047 Uiso 1 1 calc R U . . .
C17 C 0.9939(5) 0.4257(3) 0.7995(2) 0.0420(8) Uani 1 1 d . . . . .
H17 H 1.012131 0.360937 0.827476 0.050 Uiso 1 1 calc R U . . .
C18 C 0.4600(4) 0.3996(3) 0.6619(2) 0.0328(6) Uani 1 1 d . . . . .
H18A H 0.441919 0.389211 0.719833 0.039 Uiso 1 1 calc R U . . .
H18B H 0.474152 0.322052 0.632486 0.039 Uiso 1 1 calc R U . . .
C19 C 0.2972(4) 0.4217(3) 0.6067(2) 0.0331(6) Uani 1 1 d . . . . .
H19A H 0.317516 0.431454 0.549085 0.040 Uiso 1 1 calc R U . . .
H19B H 0.288683 0.501534 0.635887 0.040 Uiso 1 1 calc R U . . .
C20 C 0.1157(4) 0.3132(3) 0.5925(2) 0.0316(6) Uani 1 1 d . . . . .
H20A H 0.123825 0.233677 0.562464 0.038 Uiso 1 1 calc R U . . .
H20B H 0.097058 0.302350 0.650267 0.038 Uiso 1 1 calc R U . . .
C21 C -0.0507(4) 0.3347(3) 0.5384(2) 0.0325(6) Uani 1 1 d . . . . .
H21A H -0.032481 0.344915 0.480492 0.039 Uiso 1 1 calc R U . . .
H21B H -0.058226 0.414601 0.568223 0.039 Uiso 1 1 calc R U . . .
C22 C -0.2327(4) 0.2268(3) 0.52466(19) 0.0312(6) Uani 1 1 d . . . . .
H22A H -0.252596 0.218300 0.582539 0.037 Uiso 1 1 calc R U . . .
H22B H -0.223810 0.146595 0.496417 0.037 Uiso 1 1 calc R U . . .
C23 C -0.3990(4) 0.2465(3) 0.46834(19) 0.0325(6) Uani 1 1 d . . . . .
H23A H -0.377594 0.257444 0.411060 0.039 Uiso 1 1 calc R U . . .
H23B H -0.410172 0.325361 0.497439 0.039 Uiso 1 1 calc R U . . .
C24 C -0.5801(4) 0.1363(3) 0.45263(19) 0.0327(6) Uani 1 1 d . . . . .
H24A H -0.568797 0.057646 0.423202 0.039 Uiso 1 1 calc R U . . .
H24B H -0.600384 0.124883 0.510033 0.039 Uiso 1 1 calc R U . . .
C25 C -0.7483(4) 0.1547(3) 0.39709(19) 0.0320(6) Uani 1 1 d . . . . .
H25A H -0.763009 0.231413 0.427543 0.038 Uiso 1 1 calc R U . . .
H25B H -0.726606 0.169176 0.340427 0.038 Uiso 1 1 calc R U . . .
C26 C -0.9262(4) 0.0418(3) 0.3794(2) 0.0329(6) Uani 1 1 d . . . . .
H26A H -0.912980 -0.033648 0.346311 0.039 Uiso 1 1 calc R U . . .
H26B H -0.943088 0.024496 0.436228 0.039 Uiso 1 1 calc R U . . .
C27 C -1.0991(4) 0.0593(3) 0.32831(19) 0.0316(6) Uani 1 1 d . . . . .
H27A H -1.114838 0.133222 0.362067 0.038 Uiso 1 1 calc R U . . .
H27B H -1.081596 0.078596 0.272011 0.038 Uiso 1 1 calc R U . . .
C28 C -1.2743(4) -0.0556(3) 0.3094(2) 0.0352(7) Uani 1 1 d . . . . .
H28A H -1.291786 -0.075386 0.365603 0.042 Uiso 1 1 calc R U . . .
H28B H -1.259414 -0.129486 0.275125 0.042 Uiso 1 1 calc R U . . .
C29 C -1.4463(4) -0.0363(3) 0.2588(2) 0.0397(7) Uani 1 1 d . . . . .
H29A H -1.432123 -0.019963 0.202066 0.060 Uiso 1 1 calc R U . . .
H29B H -1.462599 0.036324 0.292565 0.060 Uiso 1 1 calc R U . . .
H29C H -1.554963 -0.112669 0.249337 0.060 Uiso 1 1 calc R U . . .
B1 B 1.5424(5) 0.7378(3) 0.8417(2) 0.0374(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.363(4) . ?
F2 B1 1.369(4) . ?
O1 C15 1.362(4) . ?
O1 C18 1.429(3) . ?
N1 N2 1.251(4) . ?
N1 C1 1.395(4) . ?
N1 B1 1.645(5) . ?
N2 C12 1.440(4) . ?
N3 C2 1.347(4) . ?
N3 C10 1.369(4) . ?
N3 B1 1.534(5) . ?
N4 C11 1.135(4) . ?
C1 C2 1.412(5) . ?
C1 C11 1.416(5) . ?
C2 C3 1.419(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.345(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.431(5) . ?
C5 C6 1.394(5) . ?
C5 C10 1.412(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.364(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.400(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.369(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.412(4) . ?
C12 C13 1.415(5) . ?
C12 C17 1.384(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.390(4) . ?
C15 C16 1.390(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.373(5) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.510(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.523(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.521(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.523(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.524(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.526(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.524(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.522(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.521(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.518(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.523(4) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O1 C18 118.4(2) . . ?
N2 N1 C1 114.4(3) . . ?
N2 N1 B1 136.4(3) . . ?
C1 N1 B1 109.2(3) . . ?
N1 N2 C12 119.7(3) . . ?
C2 N3 C10 121.5(3) . . ?
C2 N3 B1 112.9(3) . . ?
C10 N3 B1 125.6(3) . . ?
N1 C1 C2 108.9(3) . . ?
N1 C1 C11 126.8(3) . . ?
C2 C1 C11 124.3(3) . . ?
N3 C2 C1 112.3(3) . . ?
N3 C2 C3 120.6(3) . . ?
C1 C2 C3 127.1(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 123.4(3) . . ?
C6 C5 C10 118.9(3) . . ?
C10 C5 C4 117.7(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.4(3) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 120.4 . . ?
C6 C7 C8 119.3(3) . . ?
C8 C7 H7 120.4 . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.5(3) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.2(3) . . ?
C10 C9 H9 120.4 . . ?
N3 C10 C5 119.9(3) . . ?
N3 C10 C9 120.5(3) . . ?
C5 C10 C9 119.6(3) . . ?
N4 C11 C1 178.5(4) . . ?
C13 C12 N2 132.7(3) . . ?
C17 C12 N2 109.1(3) . . ?
C17 C12 C13 118.2(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
O1 C15 C14 115.0(3) . . ?
O1 C15 C16 125.3(3) . . ?
C16 C15 C14 119.7(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C12 C17 H17 119.1 . . ?
C16 C17 C12 121.8(3) . . ?
C16 C17 H17 119.1 . . ?
O1 C18 H18A 110.3 . . ?
O1 C18 H18B 110.3 . . ?
O1 C18 C19 106.9(2) . . ?
H18A C18 H18B 108.6 . . ?
C19 C18 H18A 110.3 . . ?
C19 C18 H18B 110.3 . . ?
C18 C19 H19A 109.2 . . ?
C18 C19 H19B 109.2 . . ?
C18 C19 C20 112.2(2) . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 H19A 109.2 . . ?
C20 C19 H19B 109.2 . . ?
C19 C20 H20A 109.0 . . ?
C19 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C21 C20 C19 113.0(2) . . ?
C21 C20 H20A 109.0 . . ?
C21 C20 H20B 109.0 . . ?
C20 C21 H21A 109.0 . . ?
C20 C21 H21B 109.0 . . ?
C20 C21 C22 113.1(2) . . ?
H21A C21 H21B 107.8 . . ?
C22 C21 H21A 109.0 . . ?
C22 C21 H21B 109.0 . . ?
C21 C22 H22A 108.9 . . ?
C21 C22 H22B 108.9 . . ?
C21 C22 C23 113.2(2) . . ?
H22A C22 H22B 107.7 . . ?
C23 C22 H22A 108.9 . . ?
C23 C22 H22B 108.9 . . ?
C22 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
C22 C23 C24 113.0(2) . . ?
H23A C23 H23B 107.8 . . ?
C24 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
C23 C24 H24A 108.8 . . ?
C23 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
C25 C24 C23 113.8(2) . . ?
C25 C24 H24A 108.8 . . ?
C25 C24 H24B 108.8 . . ?
C24 C25 H25A 109.0 . . ?
C24 C25 H25B 109.0 . . ?
H25A C25 H25B 107.8 . . ?
C26 C25 C24 112.9(2) . . ?
C26 C25 H25A 109.0 . . ?
C26 C25 H25B 109.0 . . ?
C25 C26 H26A 108.6 . . ?
C25 C26 H26B 108.6 . . ?
H26A C26 H26B 107.6 . . ?
C27 C26 C25 114.6(2) . . ?
C27 C26 H26A 108.6 . . ?
C27 C26 H26B 108.6 . . ?
C26 C27 H27A 108.8 . . ?
C26 C27 H27B 108.8 . . ?
H27A C27 H27B 107.7 . . ?
C28 C27 C26 113.7(2) . . ?
C28 C27 H27A 108.8 . . ?
C28 C27 H27B 108.8 . . ?
C27 C28 H28A 109.0 . . ?
C27 C28 H28B 109.0 . . ?
C27 C28 C29 113.1(3) . . ?
H28A C28 H28B 107.8 . . ?
C29 C28 H28A 109.0 . . ?
C29 C28 H28B 109.0 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
F1 B1 F2 113.4(3) . . ?
F1 B1 N1 111.4(3) . . ?
F1 B1 N3 111.4(3) . . ?
F2 B1 N1 110.0(3) . . ?
F2 B1 N3 112.7(3) . . ?
N3 B1 N1 96.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C15 C16 C17 178.9(3) . . . . ?
O1 C18 C19 C20 -178.6(2) . . . . ?
N1 N2 C12 C13 5.2(5) . . . . ?
N1 N2 C12 C17 -176.4(3) . . . . ?
N1 C1 C2 N3 -0.7(3) . . . . ?
N1 C1 C2 C3 179.3(3) . . . . ?
N2 N1 C1 C2 -178.8(3) . . . . ?
N2 N1 C1 C11 2.7(4) . . . . ?
N2 N1 B1 F1 -64.9(5) . . . . ?
N2 N1 B1 F2 61.8(5) . . . . ?
N2 N1 B1 N3 178.9(3) . . . . ?
N2 C12 C13 C14 177.1(3) . . . . ?
N2 C12 C17 C16 -177.3(3) . . . . ?
N3 C2 C3 C4 -0.9(4) . . . . ?
C1 N1 N2 C12 -178.3(3) . . . . ?
C1 N1 B1 F1 116.1(3) . . . . ?
C1 N1 B1 F2 -117.2(3) . . . . ?
C1 N1 B1 N3 -0.1(3) . . . . ?
C1 C2 C3 C4 179.1(3) . . . . ?
C2 N3 C10 C5 -0.5(4) . . . . ?
C2 N3 C10 C9 179.8(3) . . . . ?
C2 N3 B1 F1 -116.5(3) . . . . ?
C2 N3 B1 F2 114.7(3) . . . . ?
C2 N3 B1 N1 -0.3(3) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C6 178.5(3) . . . . ?
C3 C4 C5 C10 -0.1(4) . . . . ?
C4 C5 C6 C7 -178.9(3) . . . . ?
C4 C5 C10 N3 0.1(4) . . . . ?
C4 C5 C10 C9 179.8(3) . . . . ?
C5 C6 C7 C8 -0.8(5) . . . . ?
C6 C5 C10 N3 -178.6(3) . . . . ?
C6 C5 C10 C9 1.2(4) . . . . ?
C6 C7 C8 C9 1.2(5) . . . . ?
C7 C8 C9 C10 -0.4(5) . . . . ?
C8 C9 C10 N3 179.0(3) . . . . ?
C8 C9 C10 C5 -0.8(4) . . . . ?
C10 N3 C2 C1 -179.1(2) . . . . ?
C10 N3 C2 C3 0.9(4) . . . . ?
C10 N3 B1 F1 63.3(4) . . . . ?
C10 N3 B1 F2 -65.5(4) . . . . ?
C10 N3 B1 N1 179.5(2) . . . . ?
C10 C5 C6 C7 -0.4(4) . . . . ?
C11 C1 C2 N3 177.8(3) . . . . ?
C11 C1 C2 C3 -2.2(5) . . . . ?
C12 C13 C14 C15 -0.4(5) . . . . ?
C13 C12 C17 C16 1.2(5) . . . . ?
C13 C14 C15 O1 -178.7(3) . . . . ?
C13 C14 C15 C16 1.6(5) . . . . ?
C14 C15 C16 C17 -1.4(5) . . . . ?
C15 O1 C18 C19 -177.0(2) . . . . ?
C15 C16 C17 C12 0.0(5) . . . . ?
C17 C12 C13 C14 -1.0(4) . . . . ?
C18 O1 C15 C14 176.3(2) . . . . ?
C18 O1 C15 C16 -4.1(4) . . . . ?
C18 C19 C20 C21 178.9(2) . . . . ?
C19 C20 C21 C22 -179.6(2) . . . . ?
C20 C21 C22 C23 -178.4(2) . . . . ?
C21 C22 C23 C24 178.4(2) . . . . ?
C22 C23 C24 C25 179.5(2) . . . . ?
C23 C24 C25 C26 177.9(2) . . . . ?
C24 C25 C26 C27 176.8(2) . . . . ?
C25 C26 C27 C28 178.5(2) . . . . ?
C26 C27 C28 C29 179.6(3) . . . . ?
B1 N1 N2 C12 2.8(5) . . . . ?
B1 N1 C1 C2 0.5(3) . . . . ?
B1 N1 C1 C11 -178.0(3) . . . . ?
B1 N3 C2 C1 0.7(3) . . . . ?
B1 N3 C2 C3 -179.3(3) . . . . ?
B1 N3 C10 C5 179.7(3) . . . . ?
B1 N3 C10 C9 0.0(4) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id AzoBF2-12C
_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 1.682
_oxdiff_exptl_absorpt_empirical_full_min 0.605
_vrf_PLAT097_ia423d              
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.60 eA-3  
RESPONSE: We believe this large electron density comes from the fact that this was 
not as good of single crystal as we usually use.  No such crystal could be found.
;
_vrf_PLAT230_ia423d              
;
PROBLEM: Hirshfeld Test Diff for    N1       --C1       .       17.0 s.u.  
RESPONSE: We believe this large electron density comes from the fact that this was 
not as good of single crystal as we usually use.  No such crystal could be found.
;
