# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2022

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

data_exp_429
_database_code_depnum_ccdc_archive 'CCDC 2151184'
loop_
_audit_author_name
_audit_author_address
'Masahiro Ikeshita'
;Nihon University
Japan
;
_audit_update_record             
;
2022-02-10 deposited with the CCDC.	2022-06-13 downloaded from the CCDC.
;
_audit_creation_date             2022-02-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 B F2 N O'
_chemical_formula_sum            'C19 H16 B F2 N O'
_chemical_formula_weight         323.14
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H16NOBF2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.7506(8)
_cell_length_b                   6.4046(6)
_cell_length_c                   14.9030(14)
_cell_angle_alpha                90
_cell_angle_beta                 101.334(8)
_cell_angle_gamma                90
_cell_volume                     818.94(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2571
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      26.2380
_cell_measurement_theta_min      2.3590
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58274
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_preparation       CH2Cl2/EtOH
_exptl_crystal_size_max          0.456
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.058
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_av_unetI/netI     0.0688
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15183
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.443
_diffrn_reflns_theta_min         2.374
_diffrn_ambient_temperature      173.15
_diffrn_detector                 'Rigaku HyPix-3000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 107.00   0.50    8.48    --   20.00  54.00 -30.00  362
  2  ω    -72.00  67.00   0.50    8.48    --   20.00  54.00-180.00  278
  3  ω     75.00 109.00   0.50    8.48    --   20.00  54.00-180.00   68
  4  ω    -70.00  -4.00   0.50    8.48    --   20.00  54.00 -60.00  132
  5  ω     15.00  53.00   0.50    8.48    --   20.00  54.00 -60.00   76
  6  ω     76.00 108.00   0.50    8.48    --   20.00  54.00 -60.00   64
  7  ω    -70.00 -15.00   0.50    8.48    --   20.00  54.00 -90.00  110
  8  ω     -3.00  58.00   0.50    8.48    --   20.00  54.00 -90.00  122
  9  ω     67.00 109.00   0.50    8.48    --   20.00  54.00 -90.00   84
 10  ω    -68.00 -43.00   0.50    8.48    --   20.00  54.00  60.00   50
 11  ω     23.00  99.00   0.50    8.48    --   20.00  54.00  60.00  152
 12  ω     -4.00  51.00   0.50    8.48    --   20.00  54.00-150.00  110
 13  ω     85.00 110.00   0.50    8.48    --   20.00  54.00-150.00   50
 14  ω    -49.00 -24.00   0.50    8.48    --   20.00  54.00   0.00   50
 15  ω     46.00  71.00   0.50    8.48    --   20.00  54.00   0.00   50
 16  ω    -68.00 109.50   0.50    8.48    --   20.00  54.00-120.00  355
;
_diffrn_measurement_device       'fixed-chi diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB mini2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0328013000
_diffrn_orient_matrix_UB_12      -0.0026989000
_diffrn_orient_matrix_UB_13      0.0474716000
_diffrn_orient_matrix_UB_21      0.0756472000
_diffrn_orient_matrix_UB_22      0.0104961000
_diffrn_orient_matrix_UB_23      -0.0099797000
_diffrn_orient_matrix_UB_31      -0.0063455000
_diffrn_orient_matrix_UB_32      0.1101490000
_diffrn_orient_matrix_UB_33      0.0020922000
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Sealed X-ray tube'
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.926
_reflns_number_gt                2632
_reflns_number_total             4710
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 889 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4710
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      0.957
_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)+(0.0540P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1235
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C11(H11)
1.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00B(H00B), C00D(H00D), C00F(H00F), C00G(H00G),
 C00H(H00H), C18(H18), C14(H14), C15(H15), C16(H16), C17(H17)
1.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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
F001 F -0.3720(2) -0.1481(3) -0.23039(13) 0.0657(5) Uani 1 1 d . . . . .
O002 O -0.6063(2) -0.2990(3) -0.30337(13) 0.0480(5) Uani 1 1 d . . . . .
F003 F -0.5548(2) -0.2316(4) -0.14827(12) 0.0752(6) Uani 1 1 d . . . . .
N004 N -0.4070(3) -0.5074(4) -0.19974(14) 0.0417(6) Uani 1 1 d . . . . .
C10 C -0.5332(3) -0.6360(5) -0.34592(17) 0.0362(6) Uani 1 1 d . . . . .
C006 C -0.6187(3) -0.4538(4) -0.36414(18) 0.0356(6) Uani 1 1 d . . . . .
C007 C -0.4282(3) -0.6564(5) -0.25974(18) 0.0393(6) Uani 1 1 d . . . . .
H007 H -0.372251 -0.783322 -0.246061 0.047 Uiso 1 1 calc R U . . .
C008 C -0.7251(3) -0.4294(4) -0.45008(18) 0.0386(6) Uani 1 1 d . . . . .
C009 C -0.7357(3) -0.5916(5) -0.51535(18) 0.0418(7) Uani 1 1 d . . . . .
C00A C -0.5488(3) -0.7987(5) -0.41196(19) 0.0454(7) Uani 1 1 d . . . . .
H00A H -0.491150 -0.924266 -0.398226 0.054 Uiso 1 1 calc R U . . .
C00B C -0.6456(3) -0.7760(5) -0.49449(19) 0.0476(7) Uani 1 1 d . . . . .
H00B H -0.653085 -0.884311 -0.538682 0.057 Uiso 1 1 calc R U . . .
C00D C -0.8362(3) -0.5628(6) -0.60195(19) 0.0568(9) Uani 1 1 d . . . . .
H00D H -0.845320 -0.669631 -0.646894 0.068 Uiso 1 1 calc R U . . .
C00F C -0.8142(3) -0.2452(5) -0.4710(2) 0.0532(8) Uani 1 1 d . . . . .
H00F H -0.808463 -0.137286 -0.426676 0.064 Uiso 1 1 calc R U . . .
C00G C -0.9199(4) -0.3819(7) -0.6208(2) 0.0673(10) Uani 1 1 d . . . . .
H00G H -0.986081 -0.364344 -0.679036 0.081 Uiso 1 1 calc R U . . .
C00H C -0.9093(3) -0.2230(6) -0.5558(3) 0.0683(10) Uani 1 1 d . . . . .
H00H H -0.968139 -0.098563 -0.570174 0.082 Uiso 1 1 calc R U . . .
B00J B -0.4873(4) -0.2909(6) -0.2199(2) 0.0447(8) Uani 1 1 d . . . . .
C11 C -0.2993(3) -0.5419(5) -0.10893(18) 0.0502(8) Uani 1 1 d . . . . .
H11 H -0.287625 -0.405012 -0.076031 0.060 Uiso 1 1 calc R U . . .
C12 C -0.3780(4) -0.6927(6) -0.0526(2) 0.0700(11) Uani 1 1 d . . . . .
H12A H -0.479408 -0.636142 -0.046282 0.105 Uiso 1 1 calc R U . . .
H12B H -0.312077 -0.710114 0.008242 0.105 Uiso 1 1 calc R U . . .
H12C H -0.392810 -0.828274 -0.083490 0.105 Uiso 1 1 calc R U . . .
C13 C -0.1379(4) -0.6065(6) -0.12297(19) 0.0555(9) Uani 1 1 d . . . . .
C18 C -0.0754(4) -0.8029(7) -0.1008(2) 0.0755(11) Uani 1 1 d . . . . .
H18 H -0.133885 -0.905010 -0.075907 0.091 Uiso 1 1 calc R U . . .
C14 C -0.0501(4) -0.4592(7) -0.1597(2) 0.0700(11) Uani 1 1 d . . . . .
H14 H -0.091802 -0.323948 -0.175017 0.084 Uiso 1 1 calc R U . . .
C15 C 0.1601(5) -0.7061(12) -0.1515(3) 0.108(2) Uani 1 1 d . . . . .
H15 H 0.261280 -0.740344 -0.161105 0.130 Uiso 1 1 calc R U . . .
C16 C 0.0975(5) -0.5084(11) -0.1740(3) 0.0959(16) Uani 1 1 d . . . . .
H16 H 0.156145 -0.407011 -0.199214 0.115 Uiso 1 1 calc R U . . .
C17 C 0.0733(5) -0.8507(10) -0.1151(3) 0.0999(16) Uani 1 1 d . . . . .
H17 H 0.115418 -0.985491 -0.099369 0.120 Uiso 1 1 calc R U . . .


_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
F001 B00J 1.392(4) . ?
O002 C006 1.333(3) . ?
O002 B00J 1.458(4) . ?
F003 B00J 1.372(4) . ?
N004 C007 1.296(4) . ?
N004 B00J 1.557(4) . ?
N004 C11 1.506(3) . ?
C10 C006 1.384(4) . ?
C10 C007 1.431(4) . ?
C10 C00A 1.422(4) . ?
C006 C008 1.437(3) . ?
C007 H007 0.9500 . ?
C008 C009 1.413(4) . ?
C008 C00F 1.415(4) . ?
C009 C00B 1.420(4) . ?
C009 C00D 1.424(4) . ?
C00A H00A 0.9500 . ?
C00A C00B 1.357(4) . ?
C00B H00B 0.9500 . ?
C00D H00D 0.9500 . ?
C00D C00G 1.370(5) . ?
C00F H00F 0.9500 . ?
C00F C00H 1.378(4) . ?
C00G H00G 0.9500 . ?
C00G C00H 1.396(5) . ?
C00H H00H 0.9500 . ?
C11 H11 1.0000 . ?
C11 C12 1.530(4) . ?
C11 C13 1.524(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.385(5) . ?
C13 C14 1.395(5) . ?
C18 H18 0.9500 . ?
C18 C17 1.392(6) . ?
C14 H14 0.9500 . ?
C14 C16 1.386(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.394(8) . ?
C15 C17 1.375(7) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

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
C006 O002 B00J 123.7(2) . . ?
C007 N004 B00J 121.6(2) . . ?
C007 N004 C11 119.4(3) . . ?
C11 N004 B00J 118.9(2) . . ?
C006 C10 C007 118.7(2) . . ?
C006 C10 C00A 120.5(2) . . ?
C00A C10 C007 120.8(3) . . ?
O002 C006 C10 121.7(2) . . ?
O002 C006 C008 118.5(2) . . ?
C10 C006 C008 119.8(2) . . ?
N004 C007 C10 122.1(3) . . ?
N004 C007 H007 118.9 . . ?
C10 C007 H007 118.9 . . ?
C009 C008 C006 118.5(2) . . ?
C009 C008 C00F 120.2(2) . . ?
C00F C008 C006 121.3(3) . . ?
C008 C009 C00B 120.1(2) . . ?
C008 C009 C00D 118.3(3) . . ?
C00B C009 C00D 121.6(3) . . ?
C10 C00A H00A 119.8 . . ?
C00B C00A C10 120.5(3) . . ?
C00B C00A H00A 119.8 . . ?
C009 C00B H00B 119.7 . . ?
C00A C00B C009 120.6(3) . . ?
C00A C00B H00B 119.7 . . ?
C009 C00D H00D 119.8 . . ?
C00G C00D C009 120.4(3) . . ?
C00G C00D H00D 119.8 . . ?
C008 C00F H00F 120.2 . . ?
C00H C00F C008 119.7(3) . . ?
C00H C00F H00F 120.2 . . ?
C00D C00G H00G 119.5 . . ?
C00D C00G C00H 120.9(3) . . ?
C00H C00G H00G 119.5 . . ?
C00F C00H C00G 120.5(3) . . ?
C00F C00H H00H 119.7 . . ?
C00G C00H H00H 119.7 . . ?
F001 B00J O002 109.9(3) . . ?
F001 B00J N004 107.3(2) . . ?
O002 B00J N004 110.7(2) . . ?
F003 B00J F001 109.7(3) . . ?
F003 B00J O002 109.2(3) . . ?
F003 B00J N004 110.1(3) . . ?
N004 C11 H11 107.3 . . ?
N004 C11 C12 108.5(2) . . ?
N004 C11 C13 110.5(2) . . ?
C12 C11 H11 107.3 . . ?
C13 C11 H11 107.3 . . ?
C13 C11 C12 115.7(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C11 123.2(3) . . ?
C18 C13 C14 119.0(3) . . ?
C14 C13 C11 117.8(3) . . ?
C13 C18 H18 120.0 . . ?
C13 C18 C17 120.0(4) . . ?
C17 C18 H18 120.0 . . ?
C13 C14 H14 119.7 . . ?
C16 C14 C13 120.6(4) . . ?
C16 C14 H14 119.7 . . ?
C16 C15 H15 120.5 . . ?
C17 C15 H15 120.5 . . ?
C17 C15 C16 119.0(4) . . ?
C14 C16 C15 120.3(5) . . ?
C14 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 H17 119.4 . . ?
C15 C17 C18 121.2(5) . . ?
C15 C17 H17 119.4 . . ?

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
O002 C006 C008 C009 178.6(2) . . . . ?
O002 C006 C008 C00F 0.7(4) . . . . ?
N004 C11 C13 C18 -112.8(3) . . . . ?
N004 C11 C13 C14 67.4(3) . . . . ?
C10 C006 C008 C009 -2.0(3) . . . . ?
C10 C006 C008 C00F -179.9(3) . . . . ?
C10 C00A C00B C009 -1.6(4) . . . . ?
C006 O002 B00J F001 103.9(3) . . . . ?
C006 O002 B00J F003 -135.8(3) . . . . ?
C006 O002 B00J N004 -14.4(4) . . . . ?
C006 C10 C007 N004 -2.3(4) . . . . ?
C006 C10 C00A C00B 1.3(4) . . . . ?
C006 C008 C009 C00B 1.7(4) . . . . ?
C006 C008 C009 C00D -177.3(2) . . . . ?
C006 C008 C00F C00H 176.8(3) . . . . ?
C007 N004 B00J F001 -108.6(3) . . . . ?
C007 N004 B00J O002 11.3(4) . . . . ?
C007 N004 B00J F003 132.1(3) . . . . ?
C007 N004 C11 C12 -71.6(3) . . . . ?
C007 N004 C11 C13 56.1(3) . . . . ?
C007 C10 C006 O002 -0.5(4) . . . . ?
C007 C10 C006 C008 -179.9(2) . . . . ?
C007 C10 C00A C00B -178.3(3) . . . . ?
C008 C009 C00B C00A 0.1(4) . . . . ?
C008 C009 C00D C00G 0.1(4) . . . . ?
C008 C00F C00H C00G 0.8(5) . . . . ?
C009 C008 C00F C00H -1.1(4) . . . . ?
C009 C00D C00G C00H -0.4(5) . . . . ?
C00A C10 C006 O002 179.9(2) . . . . ?
C00A C10 C006 C008 0.6(4) . . . . ?
C00A C10 C007 N004 177.2(3) . . . . ?
C00B C009 C00D C00G -178.9(3) . . . . ?
C00D C009 C00B C00A 179.0(3) . . . . ?
C00D C00G C00H C00F -0.1(5) . . . . ?
C00F C008 C009 C00B 179.7(2) . . . . ?
C00F C008 C009 C00D 0.7(4) . . . . ?
B00J O002 C006 C10 10.0(4) . . . . ?
B00J O002 C006 C008 -170.7(2) . . . . ?
B00J N004 C007 C10 -3.7(4) . . . . ?
B00J N004 C11 C12 109.7(3) . . . . ?
B00J N004 C11 C13 -122.5(3) . . . . ?
C11 N004 C007 C10 177.7(2) . . . . ?
C11 N004 B00J F001 70.0(3) . . . . ?
C11 N004 B00J O002 -170.1(2) . . . . ?
C11 N004 B00J F003 -49.3(3) . . . . ?
C11 C13 C18 C17 -179.6(3) . . . . ?
C11 C13 C14 C16 179.9(3) . . . . ?
C12 C11 C13 C18 10.8(4) . . . . ?
C12 C11 C13 C14 -169.0(3) . . . . ?
C13 C18 C17 C15 -0.3(6) . . . . ?
C13 C14 C16 C15 -0.2(6) . . . . ?
C18 C13 C14 C16 0.1(5) . . . . ?
C14 C13 C18 C17 0.2(5) . . . . ?
C16 C15 C17 C18 0.2(6) . . . . ?
C17 C15 C16 C14 0.1(7) . . . . ?

_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 1.572
_oxdiff_exptl_absorpt_empirical_full_min 0.736
####################################################################### 
# 
# 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_exp_438
_database_code_depnum_ccdc_archive 'CCDC 2151187'
loop_
_audit_author_name
_audit_author_address
'Masahiro Ikeshita'
;Nihon University
Japan
;
_audit_update_record             
;
2022-02-10 deposited with the CCDC.	2022-06-13 downloaded from the CCDC.
;
_audit_creation_date             2021-12-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 B F2 N O'
_chemical_formula_sum            'C23 H18 B F2 N O'
_chemical_formula_weight         373.19
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C23H18NOF2B
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   9.7997(5)
_cell_length_b                   16.3983(8)
_cell_length_c                   22.9360(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3685.8(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6549
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      26.0520
_cell_measurement_theta_min      2.2330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1552
_exptl_crystal_preparation       CH2Cl2/EtOH
_exptl_crystal_size_max          0.455
_exptl_crystal_size_mid          0.412
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            38018
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         30.356
_diffrn_reflns_theta_min         2.167
_diffrn_ambient_temperature      173.15
_diffrn_detector                 'Rigaku HyPix-3000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 -12.00   0.50    2.72    --   20.00  54.00 120.00  124
  2  ω     -6.00  20.00   0.50    2.72    --   20.00  54.00 120.00   52
  3  ω     36.00  62.00   0.50    2.72    --   20.00  54.00 120.00   52
  4  ω    -59.00 -31.00   0.50    2.72    --   20.00  54.00-150.00   56
  5  ω    -24.00  16.00   0.50    2.72    --   20.00  54.00-150.00   80
  6  ω    -70.00   8.00   0.50    2.72    --   20.00  54.00   0.00  156
  7  ω     39.00 100.00   0.50    2.72    --   20.00  54.00   0.00  122
  8  ω    -69.00  56.00   0.50    2.72    --   20.00  54.00 150.00  250
  9  ω    -74.00 -49.00   0.50    2.72    --   20.00  54.00  90.00   50
 10  ω     12.00  37.00   0.50    2.72    --   20.00  54.00  90.00   50
 11  ω    -67.00  29.00   0.50    2.72    --   20.00  54.00  60.00  192
;
_diffrn_measurement_device       'fixed-chi diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB mini2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0057147000
_diffrn_orient_matrix_UB_12      0.0364121000
_diffrn_orient_matrix_UB_13      -0.0165144000
_diffrn_orient_matrix_UB_21      -0.0008098000
_diffrn_orient_matrix_UB_22      0.0232520000
_diffrn_orient_matrix_UB_23      0.0260709000
_diffrn_orient_matrix_UB_31      0.0721523000
_diffrn_orient_matrix_UB_32      -0.0026175000
_diffrn_orient_matrix_UB_33      0.0016236000
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Sealed X-ray tube'
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                7277
_reflns_number_total             10595
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.839
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 2445 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_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     507
_refine_ls_number_reflns         10595
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0591
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0900P)²+0.3980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1493
_refine_ls_wR_factor_ref         0.1696
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C00J(H00J), C00L(H00L)
1.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00F(H00F), C00I(H00I), C00M(H00M), C00N(H00N), C00P(H00P),
 C00S(H00S), C00T(H00T), C00U(H00U), C00X(H00X), C00Y(H00Y), C010(H010),
 C011(H011), C012(H012), C013(H013), C014(H014), C015(H015), C016(H016),
 C018(H018), C019(H019), C01A(H01M), C01B(H01B), C01C(H01C), C01F(H01F),
 C01G(H01N), C01H(H01H), C01I(H01I), C01J(H01J)
1.c Idealised Me refined as rotating group:
 C017(H01G,H01K,H01L), C01D(H01A,H01D,H01E)
;
_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
O001 O 0.4304(2) 0.21893(13) 0.61146(10) 0.0371(5) Uani 1 1 d . . . . .
F4 F 0.4337(2) 0.31352(16) 0.53597(12) 0.0685(7) Uani 1 1 d . . . . .
F3 F 0.4049(2) 0.35651(14) 0.62879(14) 0.0734(8) Uani 1 1 d . . . . .
O004 O 0.2023(2) 0.74768(16) 0.60791(11) 0.0469(6) Uani 1 1 d . . . . .
N005 N 0.4079(3) 0.67826(16) 0.64567(11) 0.0337(6) Uani 1 1 d . . . . .
N006 N 0.2174(3) 0.28942(17) 0.58181(11) 0.0343(6) Uani 1 1 d . . . . .
F2 F 0.1844(3) 0.6263(2) 0.6546(3) 0.149(2) Uani 1 1 d . . . . .
C008 C 0.3617(3) 0.14932(18) 0.61886(13) 0.0331(6) Uani 1 1 d . . . . .
C009 C 0.2776(3) 0.78763(19) 0.56926(13) 0.0324(6) Uani 1 1 d . . . . .
C00A C 0.4764(3) 0.71296(18) 0.60467(13) 0.0318(6) Uani 1 1 d . . . . .
H00A H 0.570628 0.700404 0.600933 0.038 Uiso 1 1 calc R U . . .
C00B C 0.2176(3) 0.85100(18) 0.53536(13) 0.0319(6) Uani 1 1 d . . . . .
C00C C 0.5740(3) 0.07542(19) 0.65774(13) 0.0347(7) Uani 1 1 d . . . . .
C00D C 0.3055(3) 0.89388(19) 0.49716(13) 0.0357(7) Uani 1 1 d . . . . .
F1 F 0.2335(4) 0.7356(3) 0.70638(13) 0.1212(16) Uani 1 1 d . . . . .
C00F C 0.6647(3) 0.1423(2) 0.65571(14) 0.0394(7) Uani 1 1 d . . . . .
H00F H 0.633514 0.192867 0.640431 0.047 Uiso 1 1 calc R U . . .
C00G C 0.6167(3) 0.6562(2) 0.70493(14) 0.0386(7) Uani 1 1 d . . . . .
C00H C 0.4170(3) 0.76973(19) 0.56433(12) 0.0314(6) Uani 1 1 d . . . . .
C00I C 0.4996(3) 0.8110(2) 0.52367(13) 0.0362(7) Uani 1 1 d . . . . .
H00I H 0.592874 0.796492 0.519262 0.043 Uiso 1 1 calc R U . . .
C00J C 0.4747(3) 0.6252(2) 0.69050(14) 0.0362(7) Uani 1 1 d . . . . .
H00J H 0.419132 0.630013 0.726918 0.043 Uiso 1 1 calc R U . . .
C00K C 0.4298(3) 0.07859(19) 0.64126(13) 0.0345(7) Uani 1 1 d . . . . .
C00L C 0.1400(3) 0.3654(2) 0.56542(14) 0.0403(7) Uani 1 1 d . . . . .
H00L H 0.198599 0.413004 0.576090 0.048 Uiso 1 1 calc R U . . .
C00M C 0.4453(4) 0.8718(2) 0.49082(14) 0.0393(7) Uani 1 1 d . . . . .
H00M H 0.500921 0.899709 0.463405 0.047 Uiso 1 1 calc R U . . .
C00N C 0.1562(3) 0.2203(2) 0.58754(14) 0.0378(7) Uani 1 1 d . . . . .
H00N H 0.061210 0.218022 0.579543 0.045 Uiso 1 1 calc R U . . .
C00O C 0.2227(3) 0.1476(2) 0.60511(14) 0.0362(7) Uani 1 1 d . . . . .
C00P C -0.0250(3) 0.8369(2) 0.57509(15) 0.0404(7) Uani 1 1 d . . . . .
H00P H -0.000347 0.789846 0.596870 0.048 Uiso 1 1 calc R U . . .
C00Q C 0.0746(3) 0.87567(19) 0.53973(13) 0.0346(6) Uani 1 1 d . . . . .
C00R C 0.0309(4) 0.9451(2) 0.50729(15) 0.0402(7) Uani 1 1 d . . . . .
C00S C 0.1257(4) 0.9887(2) 0.47160(15) 0.0451(8) Uani 1 1 d . . . . .
H00S H 0.096625 1.036471 0.451769 0.054 Uiso 1 1 calc R U . . .
C00T C 0.1449(4) 0.0751(2) 0.61394(16) 0.0450(8) Uani 1 1 d . . . . .
H00T H 0.050224 0.074222 0.605087 0.054 Uiso 1 1 calc R U . . .
C00U C 0.2553(4) 0.9632(2) 0.46564(15) 0.0426(8) Uani 1 1 d . . . . .
H00U H 0.314869 0.991611 0.440043 0.051 Uiso 1 1 calc R U . . .
C00V C 0.3474(4) 0.00741(19) 0.64843(13) 0.0404(8) Uani 1 1 d . . . . .
C00W C 0.6270(4) 0.0005(2) 0.67995(15) 0.0441(8) Uani 1 1 d . . . . .
C00X C 0.4083(5) -0.0658(2) 0.66992(16) 0.0531(10) Uani 1 1 d . . . . .
H00X H 0.353541 -0.113233 0.673920 0.064 Uiso 1 1 calc R U . . .
C00Y C 0.7969(4) 0.1362(2) 0.67528(15) 0.0477(8) Uani 1 1 d . . . . .
H00Y H 0.854997 0.182542 0.673534 0.057 Uiso 1 1 calc R U . . .
C00Z C 0.0097(3) 0.3722(2) 0.60060(17) 0.0437(8) Uani 1 1 d . . . . .
C010 C 0.6311(4) 0.7224(2) 0.74236(15) 0.0445(8) Uani 1 1 d . . . . .
H010 H 0.552016 0.746359 0.759124 0.053 Uiso 1 1 calc R U . . .
C011 C -0.1562(4) 0.8659(3) 0.57848(17) 0.0497(9) Uani 1 1 d . . . . .
H011 H -0.219877 0.839077 0.603143 0.060 Uiso 1 1 calc R U . . .
C012 C 0.7636(5) -0.0036(3) 0.69945(17) 0.0554(10) Uani 1 1 d . . . . .
H012 H 0.797988 -0.053708 0.714082 0.067 Uiso 1 1 calc R U . . .
C013 C 0.2070(4) 0.0080(2) 0.63494(16) 0.0463(8) Uani 1 1 d . . . . .
H013 H 0.154884 -0.040131 0.640810 0.056 Uiso 1 1 calc R U . . .
C014 C 0.8470(4) 0.0629(3) 0.69772(16) 0.0545(10) Uani 1 1 d . . . . .
H014 H 0.938180 0.059344 0.711604 0.065 Uiso 1 1 calc R U . . .
C015 C -0.1980(4) 0.9336(3) 0.54656(19) 0.0557(10) Uani 1 1 d . . . . .
H015 H -0.289465 0.952488 0.549036 0.067 Uiso 1 1 calc R U . . .
C016 C -0.1064(4) 0.9725(2) 0.51186(18) 0.0521(9) Uani 1 1 d . . . . .
H016 H -0.134634 1.018902 0.490199 0.063 Uiso 1 1 calc R U . . .
C017 C 0.4672(4) 0.5362(2) 0.67121(18) 0.0518(9) Uani 1 1 d . . . . .
H01G H 0.371650 0.520938 0.664880 0.078 Uiso 1 1 calc R U . . .
H01K H 0.506702 0.501353 0.701523 0.078 Uiso 1 1 calc R U . . .
H01L H 0.518397 0.529263 0.634851 0.078 Uiso 1 1 calc R U . . .
C018 C 0.7348(4) 0.6213(3) 0.68181(18) 0.0576(10) Uani 1 1 d . . . . .
H018 H 0.727541 0.574938 0.657203 0.069 Uiso 1 1 calc R U . . .
C019 C 0.7576(5) 0.7539(3) 0.75562(17) 0.0572(10) Uani 1 1 d . . . . .
H019 H 0.765327 0.798703 0.781686 0.069 Uiso 1 1 calc R U . . .
C01A C 0.8745(5) 0.7200(3) 0.7307(2) 0.0676(13) Uani 1 1 d . . . . .
H01M H 0.961774 0.742523 0.738844 0.081 Uiso 1 1 calc R U . . .
C01B C -0.1150(4) 0.3418(2) 0.5801(2) 0.0595(11) Uani 1 1 d . . . . .
H01B H -0.120536 0.317307 0.542652 0.071 Uiso 1 1 calc R U . . .
C01C C 0.5403(5) -0.0694(2) 0.68457(17) 0.0539(10) Uani 1 1 d . . . . .
H01C H 0.577153 -0.119450 0.698318 0.065 Uiso 1 1 calc R U . . .
C01D C 0.1209(5) 0.3674(3) 0.49945(16) 0.0590(11) Uani 1 1 d . . . . .
H01A H 0.210382 0.367029 0.480367 0.089 Uiso 1 1 calc R U . . .
H01D H 0.071479 0.417068 0.488505 0.089 Uiso 1 1 calc R U . . .
H01E H 0.068615 0.319511 0.487094 0.089 Uiso 1 1 calc R U . . .
B2 B 0.3754(4) 0.2953(2) 0.59025(19) 0.0408(9) Uani 1 1 d . . . . .
C01F C 0.0144(5) 0.4083(3) 0.6547(2) 0.0618(11) Uani 1 1 d . . . . .
H01F H 0.097959 0.430102 0.668709 0.074 Uiso 1 1 calc R U . . .
C01G C 0.8625(4) 0.6534(4) 0.6942(2) 0.0716(13) Uani 1 1 d . . . . .
H01N H 0.941822 0.629498 0.677634 0.086 Uiso 1 1 calc R U . . .
C01H C -0.2308(5) 0.3475(3) 0.6150(4) 0.085(2) Uani 1 1 d . . . . .
H01H H -0.315354 0.327358 0.600811 0.102 Uiso 1 1 calc R U . . .
C01I C -0.2253(6) 0.3813(4) 0.6688(4) 0.101(2) Uani 1 1 d . . . . .
H01I H -0.304727 0.383300 0.692498 0.122 Uiso 1 1 calc R U . . .
C01J C -0.1029(7) 0.4132(4) 0.6890(3) 0.0922(19) Uani 1 1 d . . . . .
H01J H -0.098909 0.438272 0.726324 0.111 Uiso 1 1 calc R U . . .
B01K B 0.2516(4) 0.6942(3) 0.6519(2) 0.0590(13) 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
O001 C008 1.336(4) . ?
O001 B2 1.448(5) . ?
F4 B2 1.402(5) . ?
F3 B2 1.368(5) . ?
O004 C009 1.326(4) . ?
O004 B01K 1.422(5) . ?
N005 C00A 1.288(4) . ?
N005 C00J 1.497(4) . ?
N005 B01K 1.561(5) . ?
N006 C00L 1.506(4) . ?
N006 C00N 1.288(4) . ?
N006 B2 1.563(4) . ?
F2 B01K 1.295(6) . ?
C008 C00K 1.433(5) . ?
C008 C00O 1.399(5) . ?
C009 C00B 1.425(4) . ?
C009 C00H 1.402(4) . ?
C00A H00A 0.9500 . ?
C00A C00H 1.436(4) . ?
C00B C00D 1.416(4) . ?
C00B C00Q 1.462(4) . ?
C00C C00F 1.413(5) . ?
C00C C00K 1.464(5) . ?
C00C C00W 1.428(5) . ?
C00D C00M 1.425(5) . ?
C00D C00U 1.434(5) . ?
F1 B01K 1.433(7) . ?
C00F H00F 0.9500 . ?
C00F C00Y 1.375(5) . ?
C00G C00J 1.519(5) . ?
C00G C010 1.391(5) . ?
C00G C018 1.395(5) . ?
C00H C00I 1.409(4) . ?
C00I H00I 0.9500 . ?
C00I C00M 1.357(5) . ?
C00J H00J 1.0000 . ?
C00J C017 1.527(5) . ?
C00K C00V 1.429(4) . ?
C00L H00L 1.0000 . ?
C00L C00Z 1.514(5) . ?
C00L C01D 1.525(5) . ?
C00M H00M 0.9500 . ?
C00N H00N 0.9500 . ?
C00N C00O 1.417(5) . ?
C00O C00T 1.427(4) . ?
C00P H00P 0.9500 . ?
C00P C00Q 1.420(5) . ?
C00P C011 1.373(5) . ?
C00Q C00R 1.426(5) . ?
C00R C00S 1.430(5) . ?
C00R C016 1.423(5) . ?
C00S H00S 0.9500 . ?
C00S C00U 1.344(5) . ?
C00T H00T 0.9500 . ?
C00T C013 1.347(5) . ?
C00U H00U 0.9500 . ?
C00V C00X 1.428(5) . ?
C00V C013 1.410(6) . ?
C00W C012 1.413(6) . ?
C00W C01C 1.431(6) . ?
C00X H00X 0.9500 . ?
C00X C01C 1.337(6) . ?
C00Y H00Y 0.9500 . ?
C00Y C014 1.398(5) . ?
C00Z C01B 1.402(5) . ?
C00Z C01F 1.375(6) . ?
C010 H010 0.9500 . ?
C010 C019 1.377(6) . ?
C011 H011 0.9500 . ?
C011 C015 1.392(6) . ?
C012 H012 0.9500 . ?
C012 C014 1.363(6) . ?
C013 H013 0.9500 . ?
C014 H014 0.9500 . ?
C015 H015 0.9500 . ?
C015 C016 1.358(6) . ?
C016 H016 0.9500 . ?
C017 H01G 0.9800 . ?
C017 H01K 0.9800 . ?
C017 H01L 0.9800 . ?
C018 H018 0.9500 . ?
C018 C01G 1.388(7) . ?
C019 H019 0.9500 . ?
C019 C01A 1.396(7) . ?
C01A H01M 0.9500 . ?
C01A C01G 1.381(7) . ?
C01B H01B 0.9500 . ?
C01B C01H 1.392(7) . ?
C01C H01C 0.9500 . ?
C01D H01A 0.9800 . ?
C01D H01D 0.9800 . ?
C01D H01E 0.9800 . ?
C01F H01F 0.9500 . ?
C01F C01J 1.396(7) . ?
C01G H01N 0.9500 . ?
C01H H01H 0.9500 . ?
C01H C01I 1.353(10) . ?
C01I H01I 0.9500 . ?
C01I C01J 1.389(10) . ?
C01J H01J 0.9500 . ?

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
C008 O001 B2 126.4(3) . . ?
C009 O004 B01K 126.2(3) . . ?
C00A N005 C00J 122.1(3) . . ?
C00A N005 B01K 120.3(3) . . ?
C00J N005 B01K 117.6(3) . . ?
C00L N006 B2 118.6(3) . . ?
C00N N006 C00L 121.2(3) . . ?
C00N N006 B2 120.2(3) . . ?
O001 C008 C00K 120.2(3) . . ?
O001 C008 C00O 118.6(3) . . ?
C00O C008 C00K 121.2(3) . . ?
O004 C009 C00B 119.7(3) . . ?
O004 C009 C00H 119.5(3) . . ?
C00H C009 C00B 120.7(3) . . ?
N005 C00A H00A 118.5 . . ?
N005 C00A C00H 123.1(3) . . ?
C00H C00A H00A 118.5 . . ?
C009 C00B C00Q 124.1(3) . . ?
C00D C00B C009 116.7(3) . . ?
C00D C00B C00Q 119.2(3) . . ?
C00F C00C C00K 124.8(3) . . ?
C00F C00C C00W 116.8(3) . . ?
C00W C00C C00K 118.3(3) . . ?
C00B C00D C00M 121.5(3) . . ?
C00B C00D C00U 119.8(3) . . ?
C00M C00D C00U 118.7(3) . . ?
C00C C00F H00F 119.2 . . ?
C00Y C00F C00C 121.7(3) . . ?
C00Y C00F H00F 119.2 . . ?
C010 C00G C00J 119.2(3) . . ?
C010 C00G C018 118.1(3) . . ?
C018 C00G C00J 122.7(3) . . ?
C009 C00H C00A 118.6(3) . . ?
C009 C00H C00I 120.8(3) . . ?
C00I C00H C00A 120.4(3) . . ?
C00H C00I H00I 120.2 . . ?
C00M C00I C00H 119.7(3) . . ?
C00M C00I H00I 120.2 . . ?
N005 C00J C00G 110.8(3) . . ?
N005 C00J H00J 106.9 . . ?
N005 C00J C017 109.6(3) . . ?
C00G C00J H00J 106.9 . . ?
C00G C00J C017 115.3(3) . . ?
C017 C00J H00J 106.9 . . ?
C008 C00K C00C 124.8(3) . . ?
C00V C00K C008 116.1(3) . . ?
C00V C00K C00C 119.1(3) . . ?
N006 C00L H00L 107.2 . . ?
N006 C00L C00Z 110.7(3) . . ?
N006 C00L C01D 109.1(3) . . ?
C00Z C00L H00L 107.2 . . ?
C00Z C00L C01D 115.1(3) . . ?
C01D C00L H00L 107.2 . . ?
C00D C00M H00M 119.8 . . ?
C00I C00M C00D 120.5(3) . . ?
C00I C00M H00M 119.8 . . ?
N006 C00N H00N 118.1 . . ?
N006 C00N C00O 123.7(3) . . ?
C00O C00N H00N 118.1 . . ?
C008 C00O C00N 119.7(3) . . ?
C008 C00O C00T 120.3(3) . . ?
C00N C00O C00T 119.7(3) . . ?
C00Q C00P H00P 119.3 . . ?
C011 C00P H00P 119.3 . . ?
C011 C00P C00Q 121.4(3) . . ?
C00P C00Q C00B 125.0(3) . . ?
C00P C00Q C00R 116.7(3) . . ?
C00R C00Q C00B 118.2(3) . . ?
C00Q C00R C00S 120.2(3) . . ?
C016 C00R C00Q 119.8(3) . . ?
C016 C00R C00S 119.9(3) . . ?
C00R C00S H00S 119.4 . . ?
C00U C00S C00R 121.1(3) . . ?
C00U C00S H00S 119.4 . . ?
C00O C00T H00T 120.3 . . ?
C013 C00T C00O 119.4(3) . . ?
C013 C00T H00T 120.3 . . ?
C00D C00U H00U 119.4 . . ?
C00S C00U C00D 121.3(3) . . ?
C00S C00U H00U 119.4 . . ?
C00X C00V C00K 119.3(3) . . ?
C013 C00V C00K 121.4(3) . . ?
C013 C00V C00X 119.3(3) . . ?
C00C C00W C01C 120.0(3) . . ?
C012 C00W C00C 119.9(3) . . ?
C012 C00W C01C 120.1(3) . . ?
C00V C00X H00X 119.0 . . ?
C01C C00X C00V 121.9(4) . . ?
C01C C00X H00X 119.0 . . ?
C00F C00Y H00Y 119.5 . . ?
C00F C00Y C014 120.9(4) . . ?
C014 C00Y H00Y 119.5 . . ?
C01B C00Z C00L 122.0(4) . . ?
C01F C00Z C00L 119.0(3) . . ?
C01F C00Z C01B 119.0(4) . . ?
C00G C010 H010 119.3 . . ?
C019 C010 C00G 121.3(4) . . ?
C019 C010 H010 119.3 . . ?
C00P C011 H011 119.3 . . ?
C00P C011 C015 121.5(4) . . ?
C015 C011 H011 119.3 . . ?
C00W C012 H012 119.3 . . ?
C014 C012 C00W 121.5(4) . . ?
C014 C012 H012 119.3 . . ?
C00T C013 C00V 121.7(3) . . ?
C00T C013 H013 119.2 . . ?
C00V C013 H013 119.2 . . ?
C00Y C014 H014 120.4 . . ?
C012 C014 C00Y 119.2(4) . . ?
C012 C014 H014 120.4 . . ?
C011 C015 H015 120.4 . . ?
C016 C015 C011 119.2(3) . . ?
C016 C015 H015 120.4 . . ?
C00R C016 H016 119.3 . . ?
C015 C016 C00R 121.3(3) . . ?
C015 C016 H016 119.3 . . ?
C00J C017 H01G 109.5 . . ?
C00J C017 H01K 109.5 . . ?
C00J C017 H01L 109.5 . . ?
H01G C017 H01K 109.5 . . ?
H01G C017 H01L 109.5 . . ?
H01K C017 H01L 109.5 . . ?
C00G C018 H018 119.5 . . ?
C01G C018 C00G 121.0(4) . . ?
C01G C018 H018 119.5 . . ?
C010 C019 H019 120.0 . . ?
C010 C019 C01A 119.9(4) . . ?
C01A C019 H019 120.0 . . ?
C019 C01A H01M 120.2 . . ?
C01G C01A C019 119.6(4) . . ?
C01G C01A H01M 120.2 . . ?
C00Z C01B H01B 120.2 . . ?
C01H C01B C00Z 119.6(5) . . ?
C01H C01B H01B 120.2 . . ?
C00W C01C H01C 119.4 . . ?
C00X C01C C00W 121.3(4) . . ?
C00X C01C H01C 119.4 . . ?
C00L C01D H01A 109.5 . . ?
C00L C01D H01D 109.5 . . ?
C00L C01D H01E 109.5 . . ?
H01A C01D H01D 109.5 . . ?
H01A C01D H01E 109.5 . . ?
H01D C01D H01E 109.5 . . ?
O001 B2 N006 110.9(3) . . ?
F4 B2 O001 109.3(3) . . ?
F4 B2 N006 107.9(3) . . ?
F3 B2 O001 109.8(3) . . ?
F3 B2 F4 109.3(3) . . ?
F3 B2 N006 109.6(3) . . ?
C00Z C01F H01F 119.8 . . ?
C00Z C01F C01J 120.5(5) . . ?
C01J C01F H01F 119.8 . . ?
C018 C01G H01N 120.0 . . ?
C01A C01G C018 120.1(4) . . ?
C01A C01G H01N 120.0 . . ?
C01B C01H H01H 119.3 . . ?
C01I C01H C01B 121.3(6) . . ?
C01I C01H H01H 119.3 . . ?
C01H C01I H01I 120.2 . . ?
C01H C01I C01J 119.5(5) . . ?
C01J C01I H01I 120.2 . . ?
C01F C01J H01J 120.0 . . ?
C01I C01J C01F 120.1(6) . . ?
C01I C01J H01J 120.0 . . ?
O004 B01K N005 111.8(3) . . ?
O004 B01K F1 106.5(4) . . ?
F2 B01K O004 113.0(4) . . ?
F2 B01K N005 111.1(4) . . ?
F2 B01K F1 107.7(4) . . ?
F1 B01K N005 106.3(4) . . ?

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
O001 C008 C00K C00C 0.2(4) . . . . ?
O001 C008 C00K C00V 179.1(3) . . . . ?
O001 C008 C00O C00N -4.2(4) . . . . ?
O001 C008 C00O C00T -178.2(3) . . . . ?
O004 C009 C00B C00D 176.8(3) . . . . ?
O004 C009 C00B C00Q -0.5(5) . . . . ?
O004 C009 C00H C00A -4.9(5) . . . . ?
O004 C009 C00H C00I 179.9(3) . . . . ?
N005 C00A C00H C009 -0.8(5) . . . . ?
N005 C00A C00H C00I 174.4(3) . . . . ?
N006 C00L C00Z C01B -93.0(4) . . . . ?
N006 C00L C00Z C01F 86.0(4) . . . . ?
N006 C00N C00O C008 1.8(5) . . . . ?
N006 C00N C00O C00T 175.9(3) . . . . ?
C008 O001 B2 F4 -113.6(3) . . . . ?
C008 O001 B2 F3 126.5(3) . . . . ?
C008 O001 B2 N006 5.2(5) . . . . ?
C008 C00K C00V C00X 179.3(3) . . . . ?
C008 C00K C00V C013 -0.9(4) . . . . ?
C008 C00O C00T C013 -0.9(5) . . . . ?
C009 O004 B01K N005 -7.0(6) . . . . ?
C009 O004 B01K F2 -133.2(4) . . . . ?
C009 O004 B01K F1 108.8(4) . . . . ?
C009 C00B C00D C00M 3.2(4) . . . . ?
C009 C00B C00D C00U -174.3(3) . . . . ?
C009 C00B C00Q C00P -4.3(5) . . . . ?
C009 C00B C00Q C00R 174.1(3) . . . . ?
C009 C00H C00I C00M 3.3(5) . . . . ?
C00A N005 C00J C00G 34.2(4) . . . . ?
C00A N005 C00J C017 -94.2(4) . . . . ?
C00A N005 B01K O004 0.9(6) . . . . ?
C00A N005 B01K F2 128.1(4) . . . . ?
C00A N005 B01K F1 -115.0(4) . . . . ?
C00A C00H C00I C00M -171.8(3) . . . . ?
C00B C009 C00H C00A 171.9(3) . . . . ?
C00B C009 C00H C00I -3.3(5) . . . . ?
C00B C00D C00M C00I -3.3(5) . . . . ?
C00B C00D C00U C00S 0.1(5) . . . . ?
C00B C00Q C00R C00S 0.1(4) . . . . ?
C00B C00Q C00R C016 -178.0(3) . . . . ?
C00C C00F C00Y C014 0.4(5) . . . . ?
C00C C00K C00V C00X -1.8(4) . . . . ?
C00C C00K C00V C013 178.0(3) . . . . ?
C00C C00W C012 C014 0.1(6) . . . . ?
C00C C00W C01C C00X -1.8(6) . . . . ?
C00D C00B C00Q C00P 178.4(3) . . . . ?
C00D C00B C00Q C00R -3.2(4) . . . . ?
C00F C00C C00K C008 2.3(5) . . . . ?
C00F C00C C00K C00V -176.6(3) . . . . ?
C00F C00C C00W C012 1.0(5) . . . . ?
C00F C00C C00W C01C 178.6(3) . . . . ?
C00F C00Y C014 C012 0.8(6) . . . . ?
C00G C010 C019 C01A 0.8(5) . . . . ?
C00G C018 C01G C01A 1.1(7) . . . . ?
C00H C009 C00B C00D 0.0(4) . . . . ?
C00H C009 C00B C00Q -177.3(3) . . . . ?
C00H C00I C00M C00D 0.0(5) . . . . ?
C00J N005 C00A C00H -174.3(3) . . . . ?
C00J N005 B01K O004 177.9(3) . . . . ?
C00J N005 B01K F2 -54.9(6) . . . . ?
C00J N005 B01K F1 62.0(4) . . . . ?
C00J C00G C010 C019 -178.4(3) . . . . ?
C00J C00G C018 C01G 177.5(4) . . . . ?
C00K C008 C00O C00N 174.9(3) . . . . ?
C00K C008 C00O C00T 0.9(5) . . . . ?
C00K C00C C00F C00Y 175.9(3) . . . . ?
C00K C00C C00W C012 -176.4(3) . . . . ?
C00K C00C C00W C01C 1.2(5) . . . . ?
C00K C00V C00X C01C 1.2(5) . . . . ?
C00K C00V C013 C00T 1.0(5) . . . . ?
C00L N006 C00N C00O -177.4(3) . . . . ?
C00L N006 B2 O001 174.3(3) . . . . ?
C00L N006 B2 F4 -66.1(4) . . . . ?
C00L N006 B2 F3 52.9(4) . . . . ?
C00L C00Z C01B C01H 178.1(3) . . . . ?
C00L C00Z C01F C01J -177.9(4) . . . . ?
C00M C00D C00U C00S -177.5(3) . . . . ?
C00N N006 C00L C00Z 45.1(4) . . . . ?
C00N N006 C00L C01D -82.5(4) . . . . ?
C00N N006 B2 O001 -7.3(5) . . . . ?
C00N N006 B2 F4 112.4(3) . . . . ?
C00N N006 B2 F3 -128.7(3) . . . . ?
C00N C00O C00T C013 -174.9(3) . . . . ?
C00O C008 C00K C00C -178.8(3) . . . . ?
C00O C008 C00K C00V 0.0(4) . . . . ?
C00O C00T C013 C00V -0.1(5) . . . . ?
C00P C00Q C00R C00S 178.6(3) . . . . ?
C00P C00Q C00R C016 0.6(5) . . . . ?
C00P C011 C015 C016 -0.8(6) . . . . ?
C00Q C00B C00D C00M -179.3(3) . . . . ?
C00Q C00B C00D C00U 3.2(4) . . . . ?
C00Q C00P C011 C015 1.2(6) . . . . ?
C00Q C00R C00S C00U 3.2(5) . . . . ?
C00Q C00R C016 C015 -0.2(6) . . . . ?
C00R C00S C00U C00D -3.3(5) . . . . ?
C00S C00R C016 C015 -178.3(4) . . . . ?
C00U C00D C00M C00I 174.3(3) . . . . ?
C00V C00X C01C C00W 0.6(6) . . . . ?
C00W C00C C00F C00Y -1.3(5) . . . . ?
C00W C00C C00K C008 179.4(3) . . . . ?
C00W C00C C00K C00V 0.6(4) . . . . ?
C00W C012 C014 C00Y -1.0(6) . . . . ?
C00X C00V C013 C00T -179.2(3) . . . . ?
C00Z C01B C01H C01I -0.7(6) . . . . ?
C00Z C01F C01J C01I 0.1(8) . . . . ?
C010 C00G C00J N005 78.8(3) . . . . ?
C010 C00G C00J C017 -156.0(3) . . . . ?
C010 C00G C018 C01G -2.1(6) . . . . ?
C010 C019 C01A C01G -1.9(6) . . . . ?
C011 C00P C00Q C00B 177.4(3) . . . . ?
C011 C00P C00Q C00R -1.1(5) . . . . ?
C011 C015 C016 C00R 0.3(6) . . . . ?
C012 C00W C01C C00X 175.7(4) . . . . ?
C013 C00V C00X C01C -178.6(4) . . . . ?
C016 C00R C00S C00U -178.7(4) . . . . ?
C018 C00G C00J N005 -100.8(4) . . . . ?
C018 C00G C00J C017 24.4(5) . . . . ?
C018 C00G C010 C019 1.2(5) . . . . ?
C019 C01A C01G C018 0.9(7) . . . . ?
C01B C00Z C01F C01J 1.2(6) . . . . ?
C01B C01H C01I C01J 1.9(8) . . . . ?
C01C C00W C012 C014 -177.4(4) . . . . ?
C01D C00L C00Z C01B 31.3(5) . . . . ?
C01D C00L C00Z C01F -149.7(4) . . . . ?
B2 O001 C008 C00K -179.0(3) . . . . ?
B2 O001 C008 C00O 0.1(5) . . . . ?
B2 N006 C00L C00Z -136.4(3) . . . . ?
B2 N006 C00L C01D 96.0(4) . . . . ?
B2 N006 C00N C00O 4.2(5) . . . . ?
C01F C00Z C01B C01H -0.9(5) . . . . ?
C01H C01I C01J C01F -1.6(8) . . . . ?
B01K O004 C009 C00B -167.7(4) . . . . ?
B01K O004 C009 C00H 9.2(5) . . . . ?
B01K N005 C00A C00H 2.5(5) . . . . ?
B01K N005 C00J C00G -142.7(4) . . . . ?
B01K N005 C00J C017 88.9(4) . . . . ?

_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 1.176
_oxdiff_exptl_absorpt_empirical_full_min 0.907
####################################################################### 
# 
# 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_exp_459
_database_code_depnum_ccdc_archive 'CCDC 2151186'
loop_
_audit_author_name
_audit_author_address
'Masahiro Ikeshita'
;Nihon University
Japan
;
_audit_update_record             
;
2022-02-10 deposited with the CCDC.	2022-06-13 downloaded from the CCDC.
;
_audit_creation_date             2021-12-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 B F2 N O'
_chemical_formula_sum            'C19 H16 B F2 N O'
_chemical_formula_weight         323.14
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H16NOBF2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   6.1678(14)
_cell_length_b                   8.1722(13)
_cell_length_c                   31.570(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1591.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1200
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      19.7160
_cell_measurement_theta_min      2.7840
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24387
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_preparation       CH2Cl2/EtOH
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1352
_diffrn_reflns_av_unetI/netI     0.2689
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            14957
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         30.543
_diffrn_reflns_theta_min         2.574
_diffrn_ambient_temperature      173.15
_diffrn_detector                 'Rigaku HyPix-3000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  25.00   0.50   67.01    --   20.00  54.00 -30.00   78
  2  ω     28.00  54.00   0.50   67.01    --   20.00  54.00 -30.00   52
  3  ω     79.00 109.00   0.50   67.01    --   20.00  54.00 -30.00   60
  4  ω    -74.00  93.00   0.50   67.01    --   20.00  54.00 -90.00  334
  5  ω    -68.00 -43.00   0.50   67.01    --   20.00  54.00 -60.00   50
  6  ω    -22.00 110.00   0.50   67.01    --   20.00  54.00 -60.00  264
  7  ω     14.00  51.00   0.50   67.01    --   20.00  54.00-120.00   74
  8  ω     83.00 108.00   0.50   67.01    --   20.00  54.00-120.00   50
  9  ω    -67.00 -41.00   0.50   67.01    --   20.00  54.00   0.00   52
 10  ω    -71.00 -46.00   0.50   67.01    --   20.00  54.00 -30.00   50
;
_diffrn_measurement_device       'fixed-chi diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB mini2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0084617000
_diffrn_orient_matrix_UB_12      0.0753078000
_diffrn_orient_matrix_UB_13      -0.0110756000
_diffrn_orient_matrix_UB_21      0.0044455000
_diffrn_orient_matrix_UB_22      -0.0430544000
_diffrn_orient_matrix_UB_23      -0.0194990000
_diffrn_orient_matrix_UB_31      -0.1144750000
_diffrn_orient_matrix_UB_32      0.0042410000
_diffrn_orient_matrix_UB_33      -0.0015501000
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Sealed X-ray tube'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                1834
_reflns_number_total             4620
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 414 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4620
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.2598
_refine_ls_R_factor_gt           0.1104
_refine_ls_restrained_S_all      1.003
_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)+(0.0410P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1626
_refine_special_details          ?
_olex2_refinement_description    
;
1. Rigid bond restraints
 C009, C00C, C00G, N004, B1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
2. Uiso/Uaniso restraints and constraints
C009 \\sim C00C \\sim N004 \\sim B1 \\sim C00G: within 1.7A with sigma of 0.001
and sigma for terminal atoms of 0.002 within 1.7A
3.a Ternary CH refined with riding coordinates:
 C00C(H00C)
3.b Aromatic/amide H refined with riding coordinates:
 C005(H005), C007(H007), C00B(H00B), C00E(H00E), C00F(H00F), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N)
3.c Idealised Me refined as rotating group:
 C00G(H00A,H00D,H00G)
;
_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
F001 F 0.8401(6) 0.9344(5) 0.68817(10) 0.0562(11) Uani 1 1 d . . . . .
F002 F 0.9325(6) 0.7072(4) 0.65150(12) 0.0548(11) Uani 1 1 d . . . . .
O1 O 0.8193(6) 0.9390(5) 0.61544(12) 0.0348(11) Uani 1 1 d . . . . .
N004 N 0.5611(8) 0.7686(5) 0.65712(14) 0.0270(8) Uani 1 1 d . U . . .
C005 C 0.3231(10) 0.8635(7) 0.55465(17) 0.0261(15) Uani 1 1 d . . . . .
H005 H 0.185388 0.813287 0.558190 0.031 Uiso 1 1 calc R U . . .
C006 C 0.3754(10) 0.9396(7) 0.51573(18) 0.0262(15) Uani 1 1 d . . . . .
C007 C 0.4218(10) 0.7787(7) 0.62647(17) 0.0250(15) Uani 1 1 d . . . . .
H007 H 0.283161 0.729823 0.629861 0.030 Uiso 1 1 calc R U . . .
C008 C 0.6763(10) 0.9377(7) 0.58270(18) 0.0253(14) Uani 1 1 d . . . . .
C009 C 0.4142(10) 0.5127(7) 0.68753(16) 0.0267(9) Uani 1 1 d . U . . .
C00A C 0.4710(9) 0.8615(6) 0.58762(18) 0.0200(14) Uani 1 1 d . . . . .
C00B C 0.7261(10) 1.0150(7) 0.54537(19) 0.0295(16) Uani 1 1 d . . . . .
H00B H 0.862342 1.068047 0.542491 0.035 Uiso 1 1 calc R U . . .
C00C C 0.5018(10) 0.6807(7) 0.69770(17) 0.0273(8) Uani 1 1 d . U . . .
H00C H 0.640579 0.663232 0.713452 0.033 Uiso 1 1 calc R U . . .
C00D C 0.5797(10) 1.0172(7) 0.51138(18) 0.0280(15) Uani 1 1 d . . . . .
C00E C 0.2120(10) 0.4587(8) 0.70110(18) 0.0362(16) Uani 1 1 d . . . . .
H00E H 0.123346 0.529234 0.717582 0.043 Uiso 1 1 calc R U . . .
C00F C 0.5381(10) 0.4058(7) 0.66341(17) 0.0354(16) Uani 1 1 d . . . . .
H00F H 0.677741 0.439398 0.654137 0.042 Uiso 1 1 calc R U . . .
C00G C 0.3641(10) 0.7896(7) 0.72506(17) 0.0312(11) Uani 1 1 d . U . . .
H00A H 0.435933 0.895767 0.728542 0.047 Uiso 1 1 calc R U . . .
H00D H 0.344184 0.738531 0.752866 0.047 Uiso 1 1 calc R U . . .
H00G H 0.222542 0.805629 0.711597 0.047 Uiso 1 1 calc R U . . .
C00H C 0.6319(11) 1.0915(8) 0.47189(19) 0.0396(18) Uani 1 1 d . . . . .
H00H H 0.767462 1.145005 0.468440 0.048 Uiso 1 1 calc R U . . .
C00I C 0.1382(11) 0.3040(8) 0.6910(2) 0.0465(19) Uani 1 1 d . . . . .
H00I H 0.001192 0.267635 0.701005 0.056 Uiso 1 1 calc R U . . .
C00J C 0.2291(11) 0.9401(7) 0.48098(19) 0.0396(17) Uani 1 1 d . . . . .
H00J H 0.091163 0.889552 0.483858 0.048 Uiso 1 1 calc R U . . .
C00K C 0.2842(13) 1.0123(8) 0.4435(2) 0.048(2) Uani 1 1 d . . . . .
H00K H 0.184790 1.012471 0.420515 0.058 Uiso 1 1 calc R U . . .
C00L C 0.4647(13) 0.2527(8) 0.6526(2) 0.054(2) Uani 1 1 d . . . . .
H00L H 0.552105 0.182424 0.635736 0.064 Uiso 1 1 calc R U . . .
C00M C 0.4892(13) 1.0864(9) 0.4390(2) 0.050(2) Uani 1 1 d . . . . .
H00M H 0.528508 1.133736 0.412629 0.060 Uiso 1 1 calc R U . . .
C00N C 0.2651(13) 0.2020(8) 0.6661(2) 0.050(2) Uani 1 1 d . . . . .
H00N H 0.213240 0.096563 0.658473 0.060 Uiso 1 1 calc R U . . .
B1 B 0.7953(11) 0.8406(9) 0.6532(2) 0.0279(9) Uani 1 1 d . U . . .


_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
F001 B1 1.372(7) . ?
F002 B1 1.381(7) . ?
O1 C008 1.359(6) . ?
O1 B1 1.445(7) . ?
N004 C007 1.297(6) . ?
N004 C00C 1.513(6) . ?
N004 B1 1.565(8) . ?
C005 H005 0.9500 . ?
C005 C006 1.415(7) . ?
C005 C00A 1.384(7) . ?
C006 C00D 1.417(7) . ?
C006 C00J 1.421(8) . ?
C007 H007 0.9500 . ?
C007 C00A 1.433(7) . ?
C008 C00A 1.420(7) . ?
C008 C00B 1.372(7) . ?
C009 C00C 1.510(7) . ?
C009 C00E 1.391(7) . ?
C009 C00F 1.389(7) . ?
C00B H00B 0.9500 . ?
C00B C00D 1.403(7) . ?
C00C H00C 1.0000 . ?
C00C C00G 1.503(7) . ?
C00D C00H 1.423(7) . ?
C00E H00E 0.9500 . ?
C00E C00I 1.381(8) . ?
C00F H00F 0.9500 . ?
C00F C00L 1.374(8) . ?
C00G H00A 0.9800 . ?
C00G H00D 0.9800 . ?
C00G H00G 0.9800 . ?
C00H H00H 0.9500 . ?
C00H C00M 1.361(8) . ?
C00I H00I 0.9500 . ?
C00I C00N 1.387(8) . ?
C00J H00J 0.9500 . ?
C00J C00K 1.365(8) . ?
C00K H00K 0.9500 . ?
C00K C00M 1.409(9) . ?
C00L H00L 0.9500 . ?
C00L C00N 1.368(9) . ?
C00M H00M 0.9500 . ?
C00N H00N 0.9500 . ?

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
C008 O1 B1 123.8(5) . . ?
C007 N004 C00C 120.1(5) . . ?
C007 N004 B1 121.9(5) . . ?
C00C N004 B1 117.9(5) . . ?
C006 C005 H005 119.7 . . ?
C00A C005 H005 119.7 . . ?
C00A C005 C006 120.6(6) . . ?
C005 C006 C00D 118.9(5) . . ?
C005 C006 C00J 121.8(6) . . ?
C00D C006 C00J 119.3(5) . . ?
N004 C007 H007 119.0 . . ?
N004 C007 C00A 121.9(6) . . ?
C00A C007 H007 119.0 . . ?
O1 C008 C00A 119.9(5) . . ?
O1 C008 C00B 120.3(5) . . ?
C00B C008 C00A 119.7(6) . . ?
C00E C009 C00C 123.0(6) . . ?
C00F C009 C00C 119.5(5) . . ?
C00F C009 C00E 117.6(6) . . ?
C005 C00A C007 120.7(5) . . ?
C005 C00A C008 120.0(5) . . ?
C008 C00A C007 119.3(5) . . ?
C008 C00B H00B 119.4 . . ?
C008 C00B C00D 121.3(6) . . ?
C00D C00B H00B 119.4 . . ?
N004 C00C H00C 106.4 . . ?
C009 C00C N004 109.8(4) . . ?
C009 C00C H00C 106.4 . . ?
C00G C00C N004 110.0(4) . . ?
C00G C00C C009 117.3(5) . . ?
C00G C00C H00C 106.4 . . ?
C006 C00D C00H 118.5(6) . . ?
C00B C00D C006 119.5(5) . . ?
C00B C00D C00H 122.0(6) . . ?
C009 C00E H00E 119.5 . . ?
C00I C00E C009 121.0(6) . . ?
C00I C00E H00E 119.5 . . ?
C009 C00F H00F 119.1 . . ?
C00L C00F C009 121.9(6) . . ?
C00L C00F H00F 119.1 . . ?
C00C C00G H00A 109.5 . . ?
C00C C00G H00D 109.5 . . ?
C00C C00G H00G 109.5 . . ?
H00A C00G H00D 109.5 . . ?
H00A C00G H00G 109.5 . . ?
H00D C00G H00G 109.5 . . ?
C00D C00H H00H 119.7 . . ?
C00M C00H C00D 120.6(6) . . ?
C00M C00H H00H 119.7 . . ?
C00E C00I H00I 120.2 . . ?
C00E C00I C00N 119.7(7) . . ?
C00N C00I H00I 120.2 . . ?
C006 C00J H00J 119.6 . . ?
C00K C00J C006 120.8(6) . . ?
C00K C00J H00J 119.6 . . ?
C00J C00K H00K 120.1 . . ?
C00J C00K C00M 119.7(7) . . ?
C00M C00K H00K 120.1 . . ?
C00F C00L H00L 120.2 . . ?
C00N C00L C00F 119.7(7) . . ?
C00N C00L H00L 120.2 . . ?
C00H C00M C00K 121.1(6) . . ?
C00H C00M H00M 119.4 . . ?
C00K C00M H00M 119.4 . . ?
C00I C00N H00N 119.9 . . ?
C00L C00N C00I 120.2(7) . . ?
C00L C00N H00N 119.9 . . ?
F001 B1 F002 110.4(5) . . ?
F001 B1 O1 109.4(5) . . ?
F001 B1 N004 109.4(5) . . ?
F002 B1 O1 110.2(5) . . ?
F002 B1 N004 105.8(5) . . ?
O1 B1 N004 111.7(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C008 C00A C005 178.4(5) . . . . ?
O1 C008 C00A C007 -3.4(8) . . . . ?
O1 C008 C00B C00D -179.1(5) . . . . ?
N004 C007 C00A C005 176.8(5) . . . . ?
N004 C007 C00A C008 -1.3(8) . . . . ?
C005 C006 C00D C00B 0.8(8) . . . . ?
C005 C006 C00D C00H 179.1(5) . . . . ?
C005 C006 C00J C00K -179.0(6) . . . . ?
C006 C005 C00A C007 -177.5(5) . . . . ?
C006 C005 C00A C008 0.7(8) . . . . ?
C006 C00D C00H C00M -0.6(9) . . . . ?
C006 C00J C00K C00M 0.4(9) . . . . ?
C007 N004 C00C C009 51.4(7) . . . . ?
C007 N004 C00C C00G -79.0(6) . . . . ?
C007 N004 B1 F001 130.8(6) . . . . ?
C007 N004 B1 F002 -110.3(6) . . . . ?
C007 N004 B1 O1 9.5(8) . . . . ?
C008 O1 B1 F001 -135.9(5) . . . . ?
C008 O1 B1 F002 102.6(6) . . . . ?
C008 O1 B1 N004 -14.6(8) . . . . ?
C008 C00B C00D C006 0.6(8) . . . . ?
C008 C00B C00D C00H -177.6(6) . . . . ?
C009 C00E C00I C00N -1.5(9) . . . . ?
C009 C00F C00L C00N -0.8(10) . . . . ?
C00A C005 C006 C00D -1.5(8) . . . . ?
C00A C005 C006 C00J 178.4(5) . . . . ?
C00A C008 C00B C00D -1.5(8) . . . . ?
C00B C008 C00A C005 0.8(8) . . . . ?
C00B C008 C00A C007 179.0(5) . . . . ?
C00B C00D C00H C00M 177.6(6) . . . . ?
C00C N004 C007 C00A 179.7(5) . . . . ?
C00C N004 B1 F001 -51.1(7) . . . . ?
C00C N004 B1 F002 67.8(6) . . . . ?
C00C N004 B1 O1 -172.4(5) . . . . ?
C00C C009 C00E C00I 179.9(5) . . . . ?
C00C C009 C00F C00L -178.8(6) . . . . ?
C00D C006 C00J C00K 0.9(9) . . . . ?
C00D C00H C00M C00K 1.9(11) . . . . ?
C00E C009 C00C N004 -124.2(5) . . . . ?
C00E C009 C00C C00G 2.2(8) . . . . ?
C00E C009 C00F C00L 0.9(8) . . . . ?
C00E C00I C00N C00L 1.6(10) . . . . ?
C00F C009 C00C N004 55.5(6) . . . . ?
C00F C009 C00C C00G -178.1(5) . . . . ?
C00F C009 C00E C00I 0.2(8) . . . . ?
C00F C00L C00N C00I -0.5(10) . . . . ?
C00J C006 C00D C00B -179.0(5) . . . . ?
C00J C006 C00D C00H -0.8(8) . . . . ?
C00J C00K C00M C00H -1.8(11) . . . . ?
B1 O1 C008 C00A 12.3(8) . . . . ?
B1 O1 C008 C00B -170.1(5) . . . . ?
B1 N004 C007 C00A -2.2(8) . . . . ?
B1 N004 C00C C009 -126.7(5) . . . . ?
B1 N004 C00C C00G 102.8(6) . . . . ?

_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 2.426
_oxdiff_exptl_absorpt_empirical_full_min 0.579
####################################################################### 
# 
# 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_exp_443
_database_code_depnum_ccdc_archive 'CCDC 2151185'
loop_
_audit_author_name
_audit_author_address
'Masahiro Ikeshita'
;Nihon University
Japan
;
_audit_update_record             
;
2022-02-10 deposited with the CCDC.	2022-06-13 downloaded from the CCDC.
;
_audit_creation_date             2021-12-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C19 H16 B F2 N O)'
_chemical_formula_sum            'C38 H32 B2 F4 N2 O2'
_chemical_formula_weight         646.27
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H16NOF2B
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.3730(4)
_cell_length_b                   13.9191(4)
_cell_length_c                   11.5437(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.664(4)
_cell_angle_gamma                90
_cell_volume                     1579.06(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8298
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      28.3140
_cell_measurement_theta_min      2.1420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_preparation       CH2Cl2/EtOH
_exptl_crystal_size_max          0.408
_exptl_crystal_size_mid          0.375
_exptl_crystal_size_min          0.305
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27219
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         30.499
_diffrn_reflns_theta_min         2.072
_diffrn_ambient_temperature      173.15
_diffrn_detector                 'Rigaku HyPix-3000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00 108.00   0.50    4.77    --   20.00  54.00  90.00  362
  2  ω    -73.00 -15.00   0.50    4.77    --   20.00  54.00 -30.00  116
  3  ω      3.00  33.00   0.50    4.77    --   20.00  54.00 -30.00   60
  4  ω    -71.00 -36.00   0.50    4.77    --   20.00  54.00-150.00   70
  5  ω    -17.00  60.00   0.50    4.77    --   20.00  54.00-150.00  154
  6  ω     73.00 110.00   0.50    4.77    --   20.00  54.00-150.00   74
  7  ω     -8.00  87.00   0.50    4.77    --   20.00  54.00 150.00  190
  8  ω    -52.00 -27.00   0.50    4.77    --   20.00  54.00-120.00   50
  9  ω    -20.00 110.00   0.50    4.77    --   20.00  54.00-120.00  260
 10  ω    -40.00 106.00   0.50    4.77    --   20.00  54.00   0.00  292
 11  ω    -45.00 -20.00   0.50    4.77    --   20.00  54.00 -60.00   50
 12  ω     -1.00  27.00   0.50    4.77    --   20.00  54.00 -60.00   56
 13  ω     68.00  94.00   0.50    4.77    --   20.00  54.00 -60.00   52
 14  ω    -69.00 -44.00   0.50    4.77    --   20.00  54.00  60.00   50
 15  ω     20.00  45.00   0.50    4.77    --   20.00  54.00  60.00   50
 16  ω    -32.00  -6.00   0.50    4.77    --   20.00  54.00-180.00   52
;
_diffrn_measurement_device       'fixed-chi diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB mini2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0236197000
_diffrn_orient_matrix_UB_12      0.0280162000
_diffrn_orient_matrix_UB_13      -0.0540292000
_diffrn_orient_matrix_UB_21      0.0252524000
_diffrn_orient_matrix_UB_22      -0.0349011000
_diffrn_orient_matrix_UB_23      -0.0319962000
_diffrn_orient_matrix_UB_31      -0.0633695000
_diffrn_orient_matrix_UB_32      -0.0243380000
_diffrn_orient_matrix_UB_33      -0.0163202000
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Sealed X-ray tube'
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                6157
_reflns_number_total             9216
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 2214 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         9216
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      0.981
_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)+(0.0520P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1091
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C00E(H00E), C00R(H00R)
1.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00D(H00D), C00K(H00K), C00M(H00M), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W),
 C00X(H00X), C00Y(H00Y), C010(H010), C011(H011), C012(H012), C013(H013),
 C014(H014), C015(H015), C016(H016), C017(H017), C018(H018), C01C(H01D)
1.c Idealised Me refined as rotating group:
 C00Z(H00A,H00B,H00C), C019(H01A,H01B,H01C)
;
_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
F001 F 0.61104(16) 0.64952(12) 0.61702(14) 0.0491(4) Uani 1 1 d . . . . .
F002 F -0.11625(15) 0.38252(12) 0.17327(15) 0.0546(5) Uani 1 1 d . . . . .
F003 F 0.42028(15) 0.60222(14) 0.65735(15) 0.0564(5) Uani 1 1 d . . . . .
F004 F 0.08132(17) 0.34303(13) 0.13898(15) 0.0590(5) Uani 1 1 d . . . . .
O005 O 0.52931(18) 0.49206(15) 0.57495(16) 0.0451(5) Uani 1 1 d . . . . .
O006 O -0.01544(18) 0.49484(15) 0.08265(15) 0.0434(5) Uani 1 1 d . . . . .
N007 N 0.09366(19) 0.45463(14) 0.29959(18) 0.0302(5) Uani 1 1 d . . . . .
N008 N 0.6416(2) 0.54439(15) 0.78828(18) 0.0316(5) Uani 1 1 d . . . . .
C009 C 0.7301(2) 0.47604(17) 0.7974(2) 0.0290(5) Uani 1 1 d . . . . .
H009 H 0.793309 0.462513 0.875689 0.035 Uiso 1 1 calc R U . . .
C00A C 0.1874(2) 0.57554(18) 0.2028(2) 0.0295(5) Uani 1 1 d . . . . .
C00B C 0.7368(2) 0.42060(18) 0.6957(2) 0.0297(5) Uani 1 1 d . . . . .
C00C C 0.2932(3) 0.64371(17) 0.2089(2) 0.0298(5) Uani 1 1 d . . . . .
C00D C 0.1780(2) 0.52506(17) 0.3078(2) 0.0279(5) Uani 1 1 d . . . . .
H00D H 0.235699 0.543822 0.386430 0.033 Uiso 1 1 calc R U . . .
C00E C 0.0849(2) 0.40494(18) 0.4118(2) 0.0330(6) Uani 1 1 d . . . . .
H00E H 0.012360 0.354908 0.383792 0.040 Uiso 1 1 calc R U . . .
C00F C 0.8463(3) 0.35438(18) 0.7051(2) 0.0315(5) Uani 1 1 d . . . . .
C00G C 0.5592(2) 0.54042(18) 0.9689(2) 0.0337(5) Uani 1 1 d . . . . .
C00H C 0.2855(3) 0.69825(19) 0.1021(2) 0.0373(6) Uani 1 1 d . . . . .
C00I C 0.0821(3) 0.5609(2) 0.0925(2) 0.0348(6) Uani 1 1 d . . . . .
C00J C 0.0381(2) 0.47494(17) 0.4915(2) 0.0308(5) Uani 1 1 d . . . . .
C00K C 0.9598(3) 0.3437(2) 0.8115(2) 0.0379(6) Uani 1 1 d . . . . .
H00K H 0.965482 0.380947 0.881900 0.046 Uiso 1 1 calc R U . . .
C00L C 0.6299(3) 0.4285(2) 0.5864(2) 0.0377(6) Uani 1 1 d . . . . .
C00M C 0.4063(3) 0.65776(19) 0.3143(2) 0.0360(6) Uani 1 1 d . . . . .
H00M H 0.413103 0.622517 0.386540 0.043 Uiso 1 1 calc R U . . .
C00N C 0.8406(3) 0.29686(19) 0.6014(2) 0.0378(6) Uani 1 1 d . . . . .
C00O C 0.7245(3) 0.3040(2) 0.4951(2) 0.0475(8) Uani 1 1 d . . . . .
H00O H 0.718346 0.263352 0.427434 0.057 Uiso 1 1 calc R U . . .
C00P C -0.0958(3) 0.5084(2) 0.4499(2) 0.0360(6) Uani 1 1 d . . . . .
H00P H -0.155404 0.486716 0.373462 0.043 Uiso 1 1 calc R U . . .
C00Q C 0.1227(3) 0.5074(2) 0.6030(2) 0.0411(6) Uani 1 1 d . . . . .
H00Q H 0.213995 0.485223 0.633244 0.049 Uiso 1 1 calc R U . . .
C00R C 0.6443(3) 0.59385(19) 0.9049(2) 0.0355(6) Uani 1 1 d . . . . .
H00R H 0.740538 0.591384 0.960540 0.043 Uiso 1 1 calc R U . . .
C00S C 0.3912(3) 0.7635(2) 0.1057(3) 0.0469(7) Uani 1 1 d . . . . .
H00S H 0.386661 0.799887 0.034833 0.056 Uiso 1 1 calc R U . . .
C00T C 0.5066(3) 0.7215(2) 0.3141(3) 0.0466(7) Uani 1 1 d . . . . .
H00T H 0.582339 0.729814 0.386006 0.056 Uiso 1 1 calc R U . . .
C00U C 0.4988(3) 0.7749(2) 0.2089(3) 0.0507(8) Uani 1 1 d . . . . .
H00U H 0.569080 0.819083 0.209928 0.061 Uiso 1 1 calc R U . . .
C00V C -0.1424(3) 0.5723(2) 0.5183(3) 0.0439(7) Uani 1 1 d . . . . .
H00V H -0.233738 0.594531 0.488745 0.053 Uiso 1 1 calc R U . . .
C00W C 0.4266(3) 0.5135(2) 0.9114(3) 0.0440(7) Uani 1 1 d . . . . .
H00W H 0.385002 0.527465 0.827067 0.053 Uiso 1 1 calc R U . . .
C00X C -0.0571(3) 0.6042(2) 0.6296(3) 0.0485(7) Uani 1 1 d . . . . .
H00X H -0.089690 0.647812 0.677121 0.058 Uiso 1 1 calc R U . . .
C00Y C 0.6224(3) 0.3667(2) 0.4873(2) 0.0453(7) Uani 1 1 d . . . . .
H00Y H 0.545675 0.369254 0.415207 0.054 Uiso 1 1 calc R U . . .
C00Z C 0.2175(3) 0.3521(2) 0.4750(3) 0.0421(6) Uani 1 1 d . . . . .
H00A H 0.238488 0.308782 0.416540 0.063 Uiso 1 1 calc R U . . .
H00B H 0.207900 0.314765 0.543718 0.063 Uiso 1 1 calc R U . . .
H00C H 0.291331 0.398830 0.505263 0.063 Uiso 1 1 calc R U . . .
C010 C 1.0624(3) 0.2799(2) 0.8145(3) 0.0466(7) Uani 1 1 d . . . . .
H010 H 1.137574 0.273099 0.887246 0.056 Uiso 1 1 calc R U . . .
C011 C 0.0738(3) 0.6188(2) -0.0100(2) 0.0467(8) Uani 1 1 d . . . . .
H011 H -0.000953 0.611685 -0.082992 0.056 Uiso 1 1 calc R U . . .
C012 C 0.0749(3) 0.5725(2) 0.6714(2) 0.0499(7) Uani 1 1 d . . . . .
H012 H 0.134226 0.595084 0.747430 0.060 Uiso 1 1 calc R U . . .
C013 C 0.1721(3) 0.6844(2) -0.0050(2) 0.0460(7) Uani 1 1 d . . . . .
H013 H 0.164897 0.722368 -0.075218 0.055 Uiso 1 1 calc R U . . .
C014 C 0.9486(3) 0.2332(2) 0.6074(3) 0.0476(8) Uani 1 1 d . . . . .
H014 H 0.945586 0.195487 0.537989 0.057 Uiso 1 1 calc R U . . .
C015 C 0.3529(3) 0.4660(2) 0.9752(3) 0.0541(8) Uani 1 1 d . . . . .
H015 H 0.261623 0.447029 0.934256 0.065 Uiso 1 1 calc R U . . .
C016 C 1.0570(4) 0.2251(2) 0.7116(3) 0.0520(8) Uani 1 1 d . . . . .
H016 H 1.129043 0.182165 0.714188 0.062 Uiso 1 1 calc R U . . .
C017 C 0.6165(3) 0.5192(3) 1.0922(3) 0.0577(8) Uani 1 1 d . . . . .
H017 H 0.708261 0.536862 1.133505 0.069 Uiso 1 1 calc R U . . .
C018 C 0.4116(4) 0.4462(2) 1.0978(3) 0.0572(9) Uani 1 1 d . . . . .
H018 H 0.361045 0.414077 1.141836 0.069 Uiso 1 1 calc R U . . .
C019 C 0.6067(3) 0.6995(2) 0.8839(3) 0.0538(8) Uani 1 1 d . . . . .
H01A H 0.666270 0.730637 0.844275 0.081 Uiso 1 1 calc R U . . .
H01B H 0.617635 0.730751 0.962595 0.081 Uiso 1 1 calc R U . . .
H01C H 0.511804 0.705298 0.831367 0.081 Uiso 1 1 calc R U . . .
B01A B 0.5472(3) 0.5748(3) 0.6561(3) 0.0394(7) Uani 1 1 d . . . . .
B01B B 0.0078(3) 0.4165(3) 0.1696(3) 0.0408(7) Uani 1 1 d . . . . .
C01C C 0.5432(4) 0.4733(3) 1.1555(3) 0.0709(11) Uani 1 1 d . . . . .
H01D H 0.584193 0.460093 1.240119 0.085 Uiso 1 1 calc R U . . .


_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
F001 B01A 1.383(4) . ?
F002 B01B 1.385(4) . ?
F003 B01A 1.375(3) . ?
F004 B01B 1.387(4) . ?
O005 C00L 1.342(3) . ?
O005 B01A 1.459(4) . ?
O006 C00I 1.344(3) . ?
O006 B01B 1.448(4) . ?
N007 C00D 1.297(3) . ?
N007 C00E 1.497(3) . ?
N007 B01B 1.572(3) . ?
N008 C009 1.303(3) . ?
N008 C00R 1.504(3) . ?
N008 B01A 1.584(3) . ?
C009 H009 0.9500 . ?
C009 C00B 1.425(3) . ?
C00A C00C 1.435(3) . ?
C00A C00D 1.431(3) . ?
C00A C00I 1.402(3) . ?
C00B C00F 1.440(4) . ?
C00B C00L 1.392(3) . ?
C00C C00H 1.428(3) . ?
C00C C00M 1.408(3) . ?
C00D H00D 0.9500 . ?
C00E H00E 1.0000 . ?
C00E C00J 1.522(3) . ?
C00E C00Z 1.524(4) . ?
C00F C00K 1.410(3) . ?
C00F C00N 1.426(3) . ?
C00G C00R 1.515(4) . ?
C00G C00W 1.374(3) . ?
C00G C017 1.388(4) . ?
C00H C00S 1.414(4) . ?
C00H C013 1.420(4) . ?
C00I C011 1.412(4) . ?
C00J C00P 1.396(3) . ?
C00J C00Q 1.381(3) . ?
C00K H00K 0.9500 . ?
C00K C010 1.378(4) . ?
C00L C00Y 1.413(4) . ?
C00M H00M 0.9500 . ?
C00M C00T 1.368(4) . ?
C00N C00O 1.421(4) . ?
C00N C014 1.413(4) . ?
C00O H00O 0.9500 . ?
C00O C00Y 1.354(4) . ?
C00P H00P 0.9500 . ?
C00P C00V 1.376(4) . ?
C00Q H00Q 0.9500 . ?
C00Q C012 1.392(4) . ?
C00R H00R 1.0000 . ?
C00R C019 1.521(4) . ?
C00S H00S 0.9500 . ?
C00S C00U 1.357(4) . ?
C00T H00T 0.9500 . ?
C00T C00U 1.405(4) . ?
C00U H00U 0.9500 . ?
C00V H00V 0.9500 . ?
C00V C00X 1.380(4) . ?
C00W H00W 0.9500 . ?
C00W C015 1.388(4) . ?
C00X H00X 0.9500 . ?
C00X C012 1.371(4) . ?
C00Y H00Y 0.9500 . ?
C00Z H00A 0.9800 . ?
C00Z H00B 0.9800 . ?
C00Z H00C 0.9800 . ?
C010 H010 0.9500 . ?
C010 C016 1.398(4) . ?
C011 H011 0.9500 . ?
C011 C013 1.357(4) . ?
C012 H012 0.9500 . ?
C013 H013 0.9500 . ?
C014 H014 0.9500 . ?
C014 C016 1.363(5) . ?
C015 H015 0.9500 . ?
C015 C018 1.378(5) . ?
C016 H016 0.9500 . ?
C017 H017 0.9500 . ?
C017 C01C 1.370(5) . ?
C018 H018 0.9500 . ?
C018 C01C 1.367(5) . ?
C019 H01A 0.9800 . ?
C019 H01B 0.9800 . ?
C019 H01C 0.9800 . ?
C01C H01D 0.9500 . ?

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
C00L O005 B01A 121.5(2) . . ?
C00I O006 B01B 120.09(19) . . ?
C00D N007 C00E 120.8(2) . . ?
C00D N007 B01B 119.2(2) . . ?
C00E N007 B01B 119.9(2) . . ?
C009 N008 C00R 116.8(2) . . ?
C009 N008 B01A 118.4(2) . . ?
C00R N008 B01A 124.6(2) . . ?
N008 C009 H009 118.4 . . ?
N008 C009 C00B 123.2(2) . . ?
C00B C009 H009 118.4 . . ?
C00D C00A C00C 122.8(2) . . ?
C00I C00A C00C 120.1(2) . . ?
C00I C00A C00D 117.0(2) . . ?
C009 C00B C00F 122.0(2) . . ?
C00L C00B C009 118.0(2) . . ?
C00L C00B C00F 119.9(2) . . ?
C00H C00C C00A 118.6(2) . . ?
C00M C00C C00A 123.1(2) . . ?
C00M C00C C00H 118.2(2) . . ?
N007 C00D C00A 122.4(2) . . ?
N007 C00D H00D 118.8 . . ?
C00A C00D H00D 118.8 . . ?
N007 C00E H00E 106.8 . . ?
N007 C00E C00J 110.30(19) . . ?
N007 C00E C00Z 110.0(2) . . ?
C00J C00E H00E 106.8 . . ?
C00J C00E C00Z 115.7(2) . . ?
C00Z C00E H00E 106.8 . . ?
C00K C00F C00B 123.5(2) . . ?
C00K C00F C00N 118.1(2) . . ?
C00N C00F C00B 118.5(2) . . ?
C00W C00G C00R 123.2(2) . . ?
C00W C00G C017 118.1(3) . . ?
C017 C00G C00R 118.6(2) . . ?
C00S C00H C00C 119.2(2) . . ?
C00S C00H C013 122.0(2) . . ?
C013 C00H C00C 118.8(2) . . ?
O006 C00I C00A 121.5(2) . . ?
O006 C00I C011 118.5(2) . . ?
C00A C00I C011 119.9(3) . . ?
C00P C00J C00E 118.7(2) . . ?
C00Q C00J C00E 122.8(2) . . ?
C00Q C00J C00P 118.5(2) . . ?
C00F C00K H00K 119.6 . . ?
C010 C00K C00F 120.8(3) . . ?
C010 C00K H00K 119.6 . . ?
O005 C00L C00B 120.6(2) . . ?
O005 C00L C00Y 118.8(2) . . ?
C00B C00L C00Y 120.5(3) . . ?
C00C C00M H00M 119.6 . . ?
C00T C00M C00C 120.8(2) . . ?
C00T C00M H00M 119.6 . . ?
C00O C00N C00F 118.8(3) . . ?
C014 C00N C00F 119.5(2) . . ?
C014 C00N C00O 121.7(2) . . ?
C00N C00O H00O 118.9 . . ?
C00Y C00O C00N 122.1(3) . . ?
C00Y C00O H00O 118.9 . . ?
C00J C00P H00P 119.6 . . ?
C00V C00P C00J 120.8(3) . . ?
C00V C00P H00P 119.6 . . ?
C00J C00Q H00Q 119.8 . . ?
C00J C00Q C012 120.4(2) . . ?
C012 C00Q H00Q 119.8 . . ?
N008 C00R C00G 111.39(19) . . ?
N008 C00R H00R 106.7 . . ?
N008 C00R C019 111.7(2) . . ?
C00G C00R H00R 106.7 . . ?
C00G C00R C019 113.1(2) . . ?
C019 C00R H00R 106.7 . . ?
C00H C00S H00S 119.5 . . ?
C00U C00S C00H 120.9(3) . . ?
C00U C00S H00S 119.5 . . ?
C00M C00T H00T 119.6 . . ?
C00M C00T C00U 120.8(3) . . ?
C00U C00T H00T 119.6 . . ?
C00S C00U C00T 120.0(3) . . ?
C00S C00U H00U 120.0 . . ?
C00T C00U H00U 120.0 . . ?
C00P C00V H00V 119.9 . . ?
C00P C00V C00X 120.3(3) . . ?
C00X C00V H00V 119.9 . . ?
C00G C00W H00W 119.7 . . ?
C00G C00W C015 120.7(3) . . ?
C015 C00W H00W 119.7 . . ?
C00V C00X H00X 120.2 . . ?
C012 C00X C00V 119.6(3) . . ?
C012 C00X H00X 120.2 . . ?
C00L C00Y H00Y 120.0 . . ?
C00O C00Y C00L 119.9(3) . . ?
C00O C00Y H00Y 120.0 . . ?
C00E C00Z H00A 109.5 . . ?
C00E C00Z H00B 109.5 . . ?
C00E C00Z H00C 109.5 . . ?
H00A C00Z H00B 109.5 . . ?
H00A C00Z H00C 109.5 . . ?
H00B C00Z H00C 109.5 . . ?
C00K C010 H010 119.7 . . ?
C00K C010 C016 120.6(3) . . ?
C016 C010 H010 119.7 . . ?
C00I C011 H011 119.8 . . ?
C013 C011 C00I 120.4(2) . . ?
C013 C011 H011 119.8 . . ?
C00Q C012 H012 119.8 . . ?
C00X C012 C00Q 120.4(3) . . ?
C00X C012 H012 119.8 . . ?
C00H C013 H013 119.0 . . ?
C011 C013 C00H 122.0(2) . . ?
C011 C013 H013 119.0 . . ?
C00N C014 H014 119.6 . . ?
C016 C014 C00N 120.8(3) . . ?
C016 C014 H014 119.6 . . ?
C00W C015 H015 119.9 . . ?
C018 C015 C00W 120.2(3) . . ?
C018 C015 H015 119.9 . . ?
C010 C016 H016 119.9 . . ?
C014 C016 C010 120.2(3) . . ?
C014 C016 H016 119.9 . . ?
C00G C017 H017 119.4 . . ?
C01C C017 C00G 121.2(3) . . ?
C01C C017 H017 119.4 . . ?
C015 C018 H018 120.4 . . ?
C01C C018 C015 119.3(3) . . ?
C01C C018 H018 120.4 . . ?
C00R C019 H01A 109.5 . . ?
C00R C019 H01B 109.5 . . ?
C00R C019 H01C 109.5 . . ?
H01A C019 H01B 109.5 . . ?
H01A C019 H01C 109.5 . . ?
H01B C019 H01C 109.5 . . ?
F001 B01A O005 111.1(2) . . ?
F001 B01A N008 107.6(2) . . ?
F003 B01A F001 110.8(3) . . ?
F003 B01A O005 107.4(2) . . ?
F003 B01A N008 111.3(2) . . ?
O005 B01A N008 108.7(2) . . ?
F002 B01B F004 110.3(3) . . ?
F002 B01B O006 109.2(2) . . ?
F002 B01B N007 109.5(2) . . ?
F004 B01B O006 111.2(2) . . ?
F004 B01B N007 107.6(2) . . ?
O006 B01B N007 109.0(2) . . ?
C017 C01C H01D 119.7 . . ?
C018 C01C C017 120.5(3) . . ?
C018 C01C H01D 119.7 . . ?

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
O005 C00L C00Y C00O 178.0(2) . . . . ?
O006 C00I C011 C013 -178.2(2) . . . . ?
N007 C00E C00J C00P 69.4(3) . . . . ?
N007 C00E C00J C00Q -110.1(3) . . . . ?
N008 C009 C00B C00F 171.6(2) . . . . ?
N008 C009 C00B C00L -11.4(4) . . . . ?
C009 N008 C00R C00G -86.1(3) . . . . ?
C009 N008 C00R C019 146.4(2) . . . . ?
C009 N008 B01A F001 -92.2(3) . . . . ?
C009 N008 B01A F003 146.2(2) . . . . ?
C009 N008 B01A O005 28.1(3) . . . . ?
C009 C00B C00F C00K -4.6(4) . . . . ?
C009 C00B C00F C00N 175.8(2) . . . . ?
C009 C00B C00L O005 5.1(4) . . . . ?
C009 C00B C00L C00Y -172.1(2) . . . . ?
C00A C00C C00H C00S -178.1(2) . . . . ?
C00A C00C C00H C013 1.4(3) . . . . ?
C00A C00C C00M C00T 177.9(2) . . . . ?
C00A C00I C011 C013 4.3(4) . . . . ?
C00B C00F C00K C010 -179.2(3) . . . . ?
C00B C00F C00N C00O -2.8(4) . . . . ?
C00B C00F C00N C014 178.4(2) . . . . ?
C00B C00L C00Y C00O -4.7(4) . . . . ?
C00C C00A C00D N007 -170.6(2) . . . . ?
C00C C00A C00I O006 177.3(2) . . . . ?
C00C C00A C00I C011 -5.2(3) . . . . ?
C00C C00H C00S C00U -0.1(4) . . . . ?
C00C C00H C013 C011 -2.4(4) . . . . ?
C00C C00M C00T C00U 0.3(4) . . . . ?
C00D N007 C00E C00J 62.8(3) . . . . ?
C00D N007 C00E C00Z -65.9(3) . . . . ?
C00D N007 B01B F002 -149.0(2) . . . . ?
C00D N007 B01B F004 91.1(3) . . . . ?
C00D N007 B01B O006 -29.6(3) . . . . ?
C00D C00A C00C C00H -173.1(2) . . . . ?
C00D C00A C00C C00M 8.5(4) . . . . ?
C00D C00A C00I O006 -6.9(3) . . . . ?
C00D C00A C00I C011 170.6(2) . . . . ?
C00E N007 C00D C00A -178.7(2) . . . . ?
C00E N007 B01B F002 35.5(3) . . . . ?
C00E N007 B01B F004 -84.4(3) . . . . ?
C00E N007 B01B O006 154.9(2) . . . . ?
C00E C00J C00P C00V -179.5(2) . . . . ?
C00E C00J C00Q C012 179.1(3) . . . . ?
C00F C00B C00L O005 -177.8(2) . . . . ?
C00F C00B C00L C00Y 5.0(4) . . . . ?
C00F C00K C010 C016 0.7(4) . . . . ?
C00F C00N C00O C00Y 3.2(4) . . . . ?
C00F C00N C014 C016 0.9(4) . . . . ?
C00G C00W C015 C018 0.7(5) . . . . ?
C00G C017 C01C C018 0.7(6) . . . . ?
C00H C00C C00M C00T -0.4(4) . . . . ?
C00H C00S C00U C00T 0.0(4) . . . . ?
C00I O006 B01B F002 156.3(2) . . . . ?
C00I O006 B01B F004 -81.8(3) . . . . ?
C00I O006 B01B N007 36.7(3) . . . . ?
C00I C00A C00C C00H 2.4(3) . . . . ?
C00I C00A C00C C00M -175.9(2) . . . . ?
C00I C00A C00D N007 13.7(3) . . . . ?
C00I C011 C013 C00H -0.4(4) . . . . ?
C00J C00P C00V C00X -0.2(4) . . . . ?
C00J C00Q C012 C00X 0.9(4) . . . . ?
C00K C00F C00N C00O 177.6(2) . . . . ?
C00K C00F C00N C014 -1.2(4) . . . . ?
C00K C010 C016 C014 -1.1(4) . . . . ?
C00L O005 B01A F001 82.9(3) . . . . ?
C00L O005 B01A F003 -155.8(2) . . . . ?
C00L O005 B01A N008 -35.3(3) . . . . ?
C00L C00B C00F C00K 178.5(2) . . . . ?
C00L C00B C00F C00N -1.1(4) . . . . ?
C00M C00C C00H C00S 0.3(4) . . . . ?
C00M C00C C00H C013 179.8(2) . . . . ?
C00M C00T C00U C00S -0.1(5) . . . . ?
C00N C00F C00K C010 0.4(4) . . . . ?
C00N C00O C00Y C00L 0.6(4) . . . . ?
C00N C014 C016 C010 0.2(4) . . . . ?
C00O C00N C014 C016 -177.8(3) . . . . ?
C00P C00J C00Q C012 -0.4(4) . . . . ?
C00P C00V C00X C012 0.6(4) . . . . ?
C00Q C00J C00P C00V 0.1(4) . . . . ?
C00R N008 C009 C00B 177.8(2) . . . . ?
C00R N008 B01A F001 82.8(3) . . . . ?
C00R N008 B01A F003 -38.7(3) . . . . ?
C00R N008 B01A O005 -156.8(2) . . . . ?
C00R C00G C00W C015 -178.9(3) . . . . ?
C00R C00G C017 C01C 178.3(3) . . . . ?
C00S C00H C013 C011 177.0(3) . . . . ?
C00V C00X C012 C00Q -0.9(4) . . . . ?
C00W C00G C00R N008 -51.4(3) . . . . ?
C00W C00G C00R C019 75.4(3) . . . . ?
C00W C00G C017 C01C -0.4(5) . . . . ?
C00W C015 C018 C01C -0.4(5) . . . . ?
C00Z C00E C00J C00P -165.0(2) . . . . ?
C00Z C00E C00J C00Q 15.5(3) . . . . ?
C013 C00H C00S C00U -179.6(3) . . . . ?
C014 C00N C00O C00Y -178.1(2) . . . . ?
C015 C018 C01C C017 -0.3(5) . . . . ?
C017 C00G C00R N008 130.0(3) . . . . ?
C017 C00G C00R C019 -103.2(3) . . . . ?
C017 C00G C00W C015 -0.3(4) . . . . ?
B01A O005 C00L C00B 20.5(4) . . . . ?
B01A O005 C00L C00Y -162.2(2) . . . . ?
B01A N008 C009 C00B -6.7(3) . . . . ?
B01A N008 C00R C00G 98.8(3) . . . . ?
B01A N008 C00R C019 -28.8(3) . . . . ?
B01B O006 C00I C00A -20.5(4) . . . . ?
B01B O006 C00I C011 162.0(2) . . . . ?
B01B N007 C00D C00A 5.8(3) . . . . ?
B01B N007 C00E C00J -121.7(2) . . . . ?
B01B N007 C00E C00Z 109.5(3) . . . . ?

_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 1.057
_oxdiff_exptl_absorpt_empirical_full_min 0.946
