# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
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data_190708_yamakou_2_autored
_database_code_depnum_ccdc_archive 'CCDC 2254253'
_audit_update_record             
;
2023-04-05 deposited with the CCDC.	2023-06-14 downloaded from the CCDC.
;
_audit_creation_date             2023-04-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
yamakou@shujitsu.ac.jp
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H29 B F2 N2'
_chemical_formula_sum            'C29 H29 B F2 N2'
_chemical_formula_weight         454.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C29 H29 B F2 N2'
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'
N N 0.0061 0.0033 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.7698(7)
_cell_length_b                   14.1930(5)
_cell_length_c                   12.6454(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.450(5)
_cell_angle_gamma                90
_cell_volume                     2344.32(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13734
_cell_measurement_temperature    130
_cell_measurement_theta_max      29.6930
_cell_measurement_theta_min      2.9630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            39741
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.884
_diffrn_reflns_theta_min         2.870
_diffrn_ambient_temperature      130
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00  77.00   0.25    5.00    --  -13.00  55.00 108.00  720
  2  ω   -103.00  77.00   0.25    5.00    --  -13.00  55.00 -36.00  720
  3  ω    -90.25  48.00   0.25    5.00    --  -13.00  55.00  36.00  553
  4  ω    -11.00  49.00   0.25    5.00    --  -13.00  55.00-108.00  240
  5  ω   -103.00  11.25   0.25    5.00    --  -13.00  55.00-180.00  457
;
_diffrn_measurement_device       'AFC11 (Right): Eulerian 3 circle'
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0108536000
_diffrn_orient_matrix_UB_12      0.0362621000
_diffrn_orient_matrix_UB_13      0.0406897000
_diffrn_orient_matrix_UB_21      0.0156443000
_diffrn_orient_matrix_UB_22      -0.0342863000
_diffrn_orient_matrix_UB_23      0.0428971000
_diffrn_orient_matrix_UB_31      0.0508203000
_diffrn_orient_matrix_UB_32      0.0027768000
_diffrn_orient_matrix_UB_33      -0.0019095000
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4636
_reflns_number_total             6294
_reflns_odcompleteness_completeness 92.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.82
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         6294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0483
_refine_ls_restrained_S_all      1.040
_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)+(0.0565P)²+0.6675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1209
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(H4AC)=1-FVAR(1)
 Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(H4C)=FVAR(1)
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=1-FVAR(2)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=FVAR(2)
 Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=1-FVAR(3)
 Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=FVAR(3)
3.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C009(H009), C00E(H00E), C00H(H00H), C00K(H00K), C00L(H00L),
 C00M(H00M), C00O(H00O), C00Q(H00Q), C00R(H00R), C00T(H00T)
3.b Idealised Me refined as rotating group:
 C00N(H00A,H00B,H00C), C00P(H00D,H00F,H00G), C00U(H00I,H00J,H00N), C1(H1A,H1B,
 H1C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C4A(H4AA,H4AB,H4AC), C1A(H1AA,H1AB,
 H1AC), C3A(H3AA,H3AB,H3AC)
;
_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 0.29805(6) 0.55288(6) 0.25070(8) 0.0332(2) Uani 1 1 d . . . . .
F002 F 0.34883(7) 0.43949(6) 0.15336(7) 0.0333(2) Uani 1 1 d . . . . .
N003 N 0.35039(8) 0.40425(7) 0.34021(9) 0.0170(2) Uani 1 1 d . . . . .
N004 N 0.47916(8) 0.51340(7) 0.30447(9) 0.0175(2) Uani 1 1 d . . . . .
C005 C 0.66357(10) 0.16254(9) 0.59982(11) 0.0190(3) Uani 1 1 d . . . . .
C006 C 0.47701(9) 0.21532(9) 0.52033(10) 0.0172(3) Uani 1 1 d . . . . .
H006 H 0.457651 0.163357 0.556584 0.021 Uiso 1 1 calc R U . . .
C007 C 0.58041(9) 0.23051(8) 0.53082(10) 0.0162(3) Uani 1 1 d . . . . .
C008 C 0.53663(9) 0.37981(9) 0.42495(10) 0.0160(2) Uani 1 1 d . . . . .
C009 C 0.60738(9) 0.31086(9) 0.48206(10) 0.0168(3) Uani 1 1 d . . . . .
H009 H 0.677317 0.319294 0.487851 0.020 Uiso 1 1 calc R U . . .
C00A C 0.29217(9) 0.27484(9) 0.41202(10) 0.0163(3) Uani 1 1 d . . . . .
C00B C 0.55954(10) 0.46880(9) 0.37822(10) 0.0165(3) Uani 1 1 d . . . . .
C00C C 0.40340(9) 0.27689(9) 0.45655(10) 0.0160(3) Uani 1 1 d . . . . .
C00D C 0.66006(10) 0.51054(9) 0.40475(10) 0.0176(3) Uani 1 1 d . . . . .
C00E C 0.21792(10) 0.21176(9) 0.42267(11) 0.0184(3) Uani 1 1 d . . . . .
H00E H 0.237126 0.159991 0.472576 0.022 Uiso 1 1 calc R U . . .
C00F C 0.26387(10) 0.35251(9) 0.33903(11) 0.0179(3) Uani 1 1 d . . . . .
C00G C 0.43371(9) 0.35735(8) 0.40882(10) 0.0156(2) Uani 1 1 d . . . . .
C00H C 0.74731(10) 0.47885(9) 0.49165(11) 0.0206(3) Uani 1 1 d . . . . .
H00H H 0.739584 0.432084 0.542142 0.025 Uiso 1 1 calc R U . . .
C00I C 0.11561(10) 0.22498(9) 0.35991(11) 0.0191(3) Uani 1 1 d . . . . .
C00J C 0.67371(11) 0.58976(9) 0.34139(11) 0.0209(3) Uani 1 1 d . . . . .
C00K C 0.49286(11) 0.59534(9) 0.25243(11) 0.0219(3) Uani 1 1 d . . . . .
H00K H 0.434406 0.626956 0.205108 0.026 Uiso 1 1 calc R U . . .
C00L C 0.58638(11) 0.63222(9) 0.26636(11) 0.0241(3) Uani 1 1 d . . . . .
H00L H 0.593375 0.686679 0.225699 0.029 Uiso 1 1 calc R U . . .
C00M C 0.09001(10) 0.30333(9) 0.28760(12) 0.0219(3) Uani 1 1 d . . . . .
H00M H 0.020228 0.312698 0.245168 0.026 Uiso 1 1 calc R U . . .
C00N C 0.62563(11) 0.05997(9) 0.58708(13) 0.0268(3) Uani 1 1 d . . . . .
H00A H 0.567354 0.054032 0.615343 0.040 Uiso 1 1 calc R U . . .
H00B H 0.681046 0.018358 0.629600 0.040 Uiso 1 1 calc R U . . .
H00C H 0.604327 0.042148 0.508170 0.040 Uiso 1 1 calc R U . . .
C00O C 0.16181(10) 0.36710(9) 0.27565(11) 0.0208(3) Uani 1 1 d . . . . .
H00O H 0.142307 0.419026 0.226016 0.025 Uiso 1 1 calc R U . . .
C00P C 0.76016(11) 0.16565(10) 0.56414(14) 0.0297(3) Uani 1 1 d . . . . .
H00D H 0.742178 0.150107 0.484750 0.044 Uiso 1 1 calc R U . . .
H00F H 0.810066 0.119833 0.607865 0.044 Uiso 1 1 calc R U . . .
H00G H 0.789913 0.228991 0.577002 0.044 Uiso 1 1 calc R U . . .
C00Q C 0.77285(11) 0.62573(10) 0.35585(12) 0.0257(3) Uani 1 1 d . . . . .
H00Q H 0.781616 0.677080 0.311538 0.031 Uiso 1 1 calc R U . . .
C00R C 0.85581(11) 0.58699(10) 0.43308(13) 0.0278(3) Uani 1 1 d . . . . .
H00R H 0.922658 0.608693 0.439281 0.033 Uiso 1 1 calc R U . . .
C00S C 0.03205(10) 0.15663(10) 0.36883(12) 0.0242(3) Uani 1 1 d . . . . .
C00T C 0.84269(10) 0.51499(10) 0.50357(12) 0.0243(3) Uani 1 1 d . . . . .
H00T H 0.900549 0.491007 0.560222 0.029 Uiso 1 1 calc R U . . .
C00U C 0.69030(12) 0.19139(11) 0.72288(12) 0.0317(3) Uani 1 1 d . . . . .
H00I H 0.715994 0.256264 0.732169 0.048 Uiso 1 1 calc R U . . .
H00J H 0.743054 0.149047 0.768944 0.048 Uiso 1 1 calc R U . . .
H00N H 0.628887 0.187265 0.746001 0.048 Uiso 1 1 calc R U . . .
B00V B 0.36262(11) 0.47637(10) 0.25885(13) 0.0200(3) Uani 1 1 d . . . . .
C1 C 0.0735(5) 0.0701(7) 0.4370(11) 0.053(3) Uani 0.471(16) 1 d . . P A 1
H1A H 0.122490 0.038621 0.407054 0.080 Uiso 0.471(16) 1 calc R U P A 1
H1B H 0.016979 0.026986 0.433678 0.080 Uiso 0.471(16) 1 calc R U P A 1
H1C H 0.107869 0.088340 0.514594 0.080 Uiso 0.471(16) 1 calc R U P A 1
C3 C -0.0318(10) 0.1243(9) 0.2561(8) 0.037(2) Uani 0.39(2) 1 d . . P A 1
H3A H -0.059334 0.179208 0.209093 0.056 Uiso 0.39(2) 1 calc R U P A 1
H3B H -0.088507 0.085644 0.262913 0.056 Uiso 0.39(2) 1 calc R U P A 1
H3C H 0.010293 0.086945 0.222137 0.056 Uiso 0.39(2) 1 calc R U P A 1
C4 C -0.0381(12) 0.2107(10) 0.4271(17) 0.067(3) Uani 0.46(2) 1 d . . P A 1
H4A H 0.003557 0.231079 0.501784 0.101 Uiso 0.46(2) 1 calc R U P A 1
H4B H -0.092472 0.168605 0.433194 0.101 Uiso 0.46(2) 1 calc R U P A 1
H4C H -0.068702 0.265977 0.382486 0.101 Uiso 0.46(2) 1 calc R U P A 1
C4A C 0.0004(10) 0.1808(7) 0.4671(7) 0.050(2) Uani 0.54(2) 1 d . . P A 2
H4AA H 0.059295 0.174992 0.534990 0.076 Uiso 0.54(2) 1 calc R U P A 2
H4AB H -0.053862 0.137733 0.471395 0.076 Uiso 0.54(2) 1 calc R U P A 2
H4AC H -0.025182 0.245708 0.460031 0.076 Uiso 0.54(2) 1 calc R U P A 2
C1A C 0.0755(3) 0.0537(3) 0.3783(9) 0.0387(17) Uani 0.529(16) 1 d . . P A 2
H1AA H 0.101512 0.041276 0.315867 0.058 Uiso 0.529(16) 1 calc R U P A 2
H1AB H 0.020925 0.008694 0.376126 0.058 Uiso 0.529(16) 1 calc R U P A 2
H1AC H 0.131310 0.046700 0.448740 0.058 Uiso 0.529(16) 1 calc R U P A 2
C3A C -0.0599(6) 0.1557(6) 0.2612(6) 0.0475(17) Uani 0.61(2) 1 d . . P A 2
H3AA H -0.095174 0.216610 0.252331 0.071 Uiso 0.61(2) 1 calc R U P A 2
H3AB H -0.107310 0.105476 0.265471 0.071 Uiso 0.61(2) 1 calc R U P A 2
H3AC H -0.035809 0.144564 0.197178 0.071 Uiso 0.61(2) 1 calc R U P A 2


_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 B00V 1.3865(17) . ?
F002 B00V 1.3889(17) . ?
N003 C00F 1.3955(16) . ?
N003 C00G 1.3719(16) . ?
N003 B00V 1.4981(18) . ?
N004 C00B 1.3573(16) . ?
N004 C00K 1.3783(16) . ?
N004 B00V 1.6119(18) . ?
C005 C007 1.5397(17) . ?
C005 C00N 1.5378(18) . ?
C005 C00P 1.5344(19) . ?
C005 C00U 1.537(2) . ?
C006 H006 0.9500 . ?
C006 C007 1.4042(17) . ?
C006 C00C 1.3871(17) . ?
C007 C009 1.4013(17) . ?
C008 C009 1.4081(17) . ?
C008 C00B 1.4704(17) . ?
C008 C00G 1.4031(17) . ?
C009 H009 0.9500 . ?
C00A C00C 1.4554(17) . ?
C00A C00E 1.3972(17) . ?
C00A C00F 1.4112(18) . ?
C00B C00D 1.4440(18) . ?
C00C C00G 1.4149(17) . ?
C00D C00H 1.4205(18) . ?
C00D C00J 1.4272(18) . ?
C00E H00E 0.9500 . ?
C00E C00I 1.3936(18) . ?
C00F C00O 1.3955(18) . ?
C00H H00H 0.9500 . ?
C00H C00T 1.3732(19) . ?
C00I C00M 1.4117(19) . ?
C00I C00S 1.5362(18) . ?
C00J C00L 1.410(2) . ?
C00J C00Q 1.4142(19) . ?
C00K H00K 0.9500 . ?
C00K C00L 1.349(2) . ?
C00L H00L 0.9500 . ?
C00M H00M 0.9500 . ?
C00M C00O 1.3836(19) . ?
C00N H00A 0.9800 . ?
C00N H00B 0.9800 . ?
C00N H00C 0.9800 . ?
C00O H00O 0.9500 . ?
C00P H00D 0.9800 . ?
C00P H00F 0.9800 . ?
C00P H00G 0.9800 . ?
C00Q H00Q 0.9500 . ?
C00Q C00R 1.362(2) . ?
C00R H00R 0.9500 . ?
C00R C00T 1.405(2) . ?
C00S C1 1.505(6) . ?
C00S C3 1.491(9) . ?
C00S C4 1.587(8) . ?
C00S C4A 1.482(7) . ?
C00S C1A 1.570(4) . ?
C00S C3A 1.538(6) . ?
C00T H00T 0.9500 . ?
C00U H00I 0.9800 . ?
C00U H00J 0.9800 . ?
C00U H00N 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4A H4AA 0.9800 . ?
C4A H4AB 0.9800 . ?
C4A H4AC 0.9800 . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 0.9800 . ?
C3A H3AA 0.9800 . ?
C3A H3AB 0.9800 . ?
C3A H3AC 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00F N003 B00V 129.30(11) . . ?
C00G N003 C00F 106.96(10) . . ?
C00G N003 B00V 120.83(11) . . ?
C00B N004 C00K 121.10(11) . . ?
C00B N004 B00V 126.64(10) . . ?
C00K N004 B00V 112.05(10) . . ?
C00N C005 C007 111.51(10) . . ?
C00P C005 C007 111.94(11) . . ?
C00P C005 C00N 107.08(11) . . ?
C00P C005 C00U 109.75(12) . . ?
C00U C005 C007 107.68(11) . . ?
C00U C005 C00N 108.84(12) . . ?
C007 C006 H006 120.3 . . ?
C00C C006 H006 120.3 . . ?
C00C C006 C007 119.39(11) . . ?
C006 C007 C005 120.49(11) . . ?
C009 C007 C005 120.41(11) . . ?
C009 C007 C006 119.03(11) . . ?
C009 C008 C00B 126.98(11) . . ?
C00G C008 C009 114.81(11) . . ?
C00G C008 C00B 118.16(11) . . ?
C007 C009 C008 123.68(11) . . ?
C007 C009 H009 118.2 . . ?
C008 C009 H009 118.2 . . ?
C00E C00A C00C 133.49(12) . . ?
C00E C00A C00F 120.31(11) . . ?
C00F C00A C00C 106.04(11) . . ?
N004 C00B C008 116.41(11) . . ?
N004 C00B C00D 118.79(11) . . ?
C00D C00B C008 124.80(11) . . ?
C006 C00C C00A 134.29(11) . . ?
C006 C00C C00G 119.77(11) . . ?
C00G C00C C00A 105.52(11) . . ?
C00H C00D C00B 124.31(11) . . ?
C00H C00D C00J 117.02(12) . . ?
C00J C00D C00B 118.66(12) . . ?
C00A C00E H00E 120.1 . . ?
C00I C00E C00A 119.84(12) . . ?
C00I C00E H00E 120.1 . . ?
N003 C00F C00A 110.24(11) . . ?
C00O C00F N003 129.00(12) . . ?
C00O C00F C00A 120.73(12) . . ?
N003 C00G C008 125.86(11) . . ?
N003 C00G C00C 111.15(11) . . ?
C008 C00G C00C 122.82(11) . . ?
C00D C00H H00H 119.6 . . ?
C00T C00H C00D 120.80(12) . . ?
C00T C00H H00H 119.6 . . ?
C00E C00I C00M 118.37(12) . . ?
C00E C00I C00S 121.26(12) . . ?
C00M C00I C00S 120.38(11) . . ?
C00L C00J C00D 118.61(12) . . ?
C00L C00J C00Q 121.04(12) . . ?
C00Q C00J C00D 120.34(13) . . ?
N004 C00K H00K 118.9 . . ?
C00L C00K N004 122.30(13) . . ?
C00L C00K H00K 118.9 . . ?
C00J C00L H00L 120.1 . . ?
C00K C00L C00J 119.85(12) . . ?
C00K C00L H00L 120.1 . . ?
C00I C00M H00M 118.5 . . ?
C00O C00M C00I 123.06(12) . . ?
C00O C00M H00M 118.5 . . ?
C005 C00N H00A 109.5 . . ?
C005 C00N H00B 109.5 . . ?
C005 C00N H00C 109.5 . . ?
H00A C00N H00B 109.5 . . ?
H00A C00N H00C 109.5 . . ?
H00B C00N H00C 109.5 . . ?
C00F C00O H00O 121.2 . . ?
C00M C00O C00F 117.70(12) . . ?
C00M C00O H00O 121.2 . . ?
C005 C00P H00D 109.5 . . ?
C005 C00P H00F 109.5 . . ?
C005 C00P H00G 109.5 . . ?
H00D C00P H00F 109.5 . . ?
H00D C00P H00G 109.5 . . ?
H00F C00P H00G 109.5 . . ?
C00J C00Q H00Q 119.9 . . ?
C00R C00Q C00J 120.22(13) . . ?
C00R C00Q H00Q 119.9 . . ?
C00Q C00R H00R 119.9 . . ?
C00Q C00R C00T 120.10(13) . . ?
C00T C00R H00R 119.9 . . ?
C00I C00S C4 108.0(3) . . ?
C00I C00S C1A 108.5(2) . . ?
C00I C00S C3A 111.5(3) . . ?
C1 C00S C00I 113.6(2) . . ?
C1 C00S C4 107.8(10) . . ?
C3 C00S C00I 110.7(4) . . ?
C3 C00S C1 107.4(7) . . ?
C3 C00S C4 109.4(9) . . ?
C4A C00S C00I 110.0(3) . . ?
C4A C00S C1A 111.0(6) . . ?
C4A C00S C3A 111.5(7) . . ?
C3A C00S C1A 104.3(5) . . ?
C00H C00T C00R 120.84(13) . . ?
C00H C00T H00T 119.6 . . ?
C00R C00T H00T 119.6 . . ?
C005 C00U H00I 109.5 . . ?
C005 C00U H00J 109.5 . . ?
C005 C00U H00N 109.5 . . ?
H00I C00U H00J 109.5 . . ?
H00I C00U H00N 109.5 . . ?
H00J C00U H00N 109.5 . . ?
F001 B00V F002 109.52(11) . . ?
F001 B00V N003 112.17(11) . . ?
F001 B00V N004 108.27(10) . . ?
F002 B00V N003 113.03(11) . . ?
F002 B00V N004 106.54(11) . . ?
N003 B00V N004 107.01(10) . . ?
C00S C1 H1A 109.5 . . ?
C00S C1 H1B 109.5 . . ?
C00S C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C00S C3 H3A 109.5 . . ?
C00S C3 H3B 109.5 . . ?
C00S C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C00S C4 H4A 109.5 . . ?
C00S C4 H4B 109.5 . . ?
C00S C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C00S C4A H4AA 109.5 . . ?
C00S C4A H4AB 109.5 . . ?
C00S C4A H4AC 109.5 . . ?
H4AA C4A H4AB 109.5 . . ?
H4AA C4A H4AC 109.5 . . ?
H4AB C4A H4AC 109.5 . . ?
C00S C1A H1AA 109.5 . . ?
C00S C1A H1AB 109.5 . . ?
C00S C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
C00S C3A H3AA 109.5 . . ?
C00S C3A H3AB 109.5 . . ?
C00S C3A H3AC 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?

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
N003 C00F C00O C00M 178.03(13) . . . . ?
N004 C00B C00D C00H 170.49(11) . . . . ?
N004 C00B C00D C00J -8.55(17) . . . . ?
N004 C00K C00L C00J -3.9(2) . . . . ?
C005 C007 C009 C008 -175.10(12) . . . . ?
C006 C007 C009 C008 1.87(19) . . . . ?
C006 C00C C00G N003 174.06(11) . . . . ?
C006 C00C C00G C008 -1.49(19) . . . . ?
C007 C006 C00C C00A 167.31(13) . . . . ?
C007 C006 C00C C00G -4.02(18) . . . . ?
C008 C00B C00D C00H -9.9(2) . . . . ?
C008 C00B C00D C00J 171.06(11) . . . . ?
C009 C008 C00B N004 164.76(12) . . . . ?
C009 C008 C00B C00D -14.9(2) . . . . ?
C009 C008 C00G N003 -168.18(12) . . . . ?
C009 C008 C00G C00C 6.70(18) . . . . ?
C00A C00C C00G N003 0.49(14) . . . . ?
C00A C00C C00G C008 -175.06(11) . . . . ?
C00A C00E C00I C00M -0.68(19) . . . . ?
C00A C00E C00I C00S 179.54(12) . . . . ?
C00A C00F C00O C00M 0.39(19) . . . . ?
C00B N004 C00K C00L 4.1(2) . . . . ?
C00B N004 B00V F001 141.17(12) . . . . ?
C00B N004 B00V F002 -101.11(14) . . . . ?
C00B N004 B00V N003 20.07(17) . . . . ?
C00B C008 C009 C007 175.58(12) . . . . ?
C00B C008 C00G N003 9.55(19) . . . . ?
C00B C008 C00G C00C -175.57(11) . . . . ?
C00B C00D C00H C00T 172.40(12) . . . . ?
C00B C00D C00J C00L 8.77(18) . . . . ?
C00B C00D C00J C00Q -172.58(12) . . . . ?
C00C C006 C007 C005 -179.19(11) . . . . ?
C00C C006 C007 C009 3.84(18) . . . . ?
C00C C00A C00E C00I -173.83(13) . . . . ?
C00C C00A C00F N003 -2.75(14) . . . . ?
C00C C00A C00F C00O 175.29(12) . . . . ?
C00D C00H C00T C00R 2.7(2) . . . . ?
C00D C00J C00L C00K -2.7(2) . . . . ?
C00D C00J C00Q C00R -2.2(2) . . . . ?
C00E C00A C00C C006 4.3(2) . . . . ?
C00E C00A C00C C00G 176.52(13) . . . . ?
C00E C00A C00F N003 -178.68(11) . . . . ?
C00E C00A C00F C00O -0.64(19) . . . . ?
C00E C00I C00M C00O 0.5(2) . . . . ?
C00E C00I C00S C1 -8.2(7) . . . . ?
C00E C00I C00S C3 -129.1(7) . . . . ?
C00E C00I C00S C4 111.2(9) . . . . ?
C00E C00I C00S C4A 82.1(6) . . . . ?
C00E C00I C00S C1A -39.5(5) . . . . ?
C00E C00I C00S C3A -153.8(5) . . . . ?
C00F N003 C00G C008 173.22(12) . . . . ?
C00F N003 C00G C00C -2.16(14) . . . . ?
C00F N003 B00V F001 60.50(18) . . . . ?
C00F N003 B00V F002 -63.93(17) . . . . ?
C00F N003 B00V N004 179.10(11) . . . . ?
C00F C00A C00C C006 -170.83(14) . . . . ?
C00F C00A C00C C00G 1.36(13) . . . . ?
C00F C00A C00E C00I 0.78(19) . . . . ?
C00G N003 C00F C00A 3.06(14) . . . . ?
C00G N003 C00F C00O -174.77(13) . . . . ?
C00G N003 B00V F001 -141.45(12) . . . . ?
C00G N003 B00V F002 94.13(14) . . . . ?
C00G N003 B00V N004 -22.84(16) . . . . ?
C00G C008 C009 C007 -6.93(18) . . . . ?
C00G C008 C00B N004 -12.66(17) . . . . ?
C00G C008 C00B C00D 167.72(12) . . . . ?
C00H C00D C00J C00L -170.34(12) . . . . ?
C00H C00D C00J C00Q 8.31(18) . . . . ?
C00I C00M C00O C00F -0.3(2) . . . . ?
C00J C00D C00H C00T -8.54(18) . . . . ?
C00J C00Q C00R C00T -4.0(2) . . . . ?
C00K N004 C00B C008 -177.42(11) . . . . ?
C00K N004 C00B C00D 2.23(18) . . . . ?
C00K N004 B00V F001 -44.04(14) . . . . ?
C00K N004 B00V F002 73.68(13) . . . . ?
C00K N004 B00V N003 -165.15(11) . . . . ?
C00L C00J C00Q C00R 176.41(13) . . . . ?
C00M C00I C00S C1 172.0(7) . . . . ?
C00M C00I C00S C3 51.1(7) . . . . ?
C00M C00I C00S C4 -68.5(9) . . . . ?
C00M C00I C00S C4A -97.7(6) . . . . ?
C00M C00I C00S C1A 140.7(4) . . . . ?
C00M C00I C00S C3A 26.4(5) . . . . ?
C00N C005 C007 C006 36.81(17) . . . . ?
C00N C005 C007 C009 -146.26(12) . . . . ?
C00P C005 C007 C006 156.75(12) . . . . ?
C00P C005 C007 C009 -26.32(17) . . . . ?
C00Q C00J C00L C00K 178.63(13) . . . . ?
C00Q C00R C00T C00H 3.8(2) . . . . ?
C00S C00I C00M C00O -179.76(13) . . . . ?
C00U C005 C007 C006 -82.53(15) . . . . ?
C00U C005 C007 C009 94.40(14) . . . . ?
B00V N003 C00F C00A 163.46(12) . . . . ?
B00V N003 C00F C00O -14.4(2) . . . . ?
B00V N003 C00G C008 10.82(19) . . . . ?
B00V N003 C00G C00C -164.56(11) . . . . ?
B00V N004 C00B C008 -3.07(18) . . . . ?
B00V N004 C00B C00D 176.58(11) . . . . ?
B00V N004 C00K C00L -170.97(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.622
_oxdiff_exptl_absorpt_empirical_full_min 0.708
####################################################################### 
# 
# 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_20180518_bf2_2q_autored
_database_code_depnum_ccdc_archive 'CCDC 2254255'
_audit_update_record             
;
2023-04-05 deposited with the CCDC.	2023-06-14 downloaded from the CCDC.
;
_audit_creation_date             2023-04-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
yamakou@shujitsu.ac.jp
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H29 B F2 N2'
_chemical_formula_sum            'C29 H29 B F2 N2'
_chemical_formula_weight         454.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C29 H29 B F2 N2'
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'
N N 0.0061 0.0033 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.9381(5)
_cell_length_b                   9.9194(3)
_cell_length_c                   11.6477(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.414(2)
_cell_angle_gamma                90
_cell_volume                     2379.30(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21378
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.0800
_cell_measurement_theta_min      2.3410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_recrystallization_method 'Recryst. from toluene-hexane'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            39597
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.972
_diffrn_reflns_theta_min         2.716
_diffrn_ambient_temperature      130
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00  77.00   0.25    5.00    --  -13.00  55.00-108.00  720
  2  ω   -103.00  77.00   0.25    5.00    --  -13.00  55.00 108.00  720
  3  ω    -25.00  35.00   0.25    5.00    --  -13.00  27.00 -36.00  240
  4  ω    -87.00  49.00   0.25    5.00    --  -13.00  55.00  36.00  544
  5  ω   -103.00  14.00   0.25    5.00    --  -13.00  55.00 -36.00  468
;
_diffrn_measurement_device       'AFC11 (Right): Eulerian 3 circle'
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0024021000
_diffrn_orient_matrix_UB_12      -0.0011218000
_diffrn_orient_matrix_UB_13      0.0615311000
_diffrn_orient_matrix_UB_21      0.0343485000
_diffrn_orient_matrix_UB_22      0.0024943000
_diffrn_orient_matrix_UB_23      0.0069458000
_diffrn_orient_matrix_UB_31      -0.0011536000
_diffrn_orient_matrix_UB_32      0.0714276000
_diffrn_orient_matrix_UB_33      0.0007026000
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5406
_reflns_number_total             6427
_reflns_odcompleteness_completeness 92.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.91
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         6427
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0423
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0675P)²+0.5293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1238
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=1-FVAR(1)
 Sof(C00W)=Sof(H00S)=Sof(H00T)=Sof(H00U)=FVAR(1)
 Sof(C00Z)=Sof(H00Z)=Sof(HB)=Sof(HC)=1-FVAR(2)
 Sof(C00Y)=Sof(H00Y)=Sof(H)=Sof(HA)=FVAR(2)
 Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=1-FVAR(3)
 Sof(C00X)=Sof(H00V)=Sof(H00W)=Sof(H00X)=FVAR(3)
3.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00E(H00E), C00I(H00I), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q)
3.b Idealised Me refined as rotating group:
 C00S(H00A,H00B,H00C), C00T(H00D,H00F,H00G), C00U(H00H,H00J,H00R), C00W(H00S,
 H00T,H00U), C00X(H00V,H00W,H00X), C00Y(H00Y,H,HA), C1(H1A,H1B,H1C), C00Z(H00Z,
 HB,HC), C2(H2A,H2B,H2C)
;
_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 0.39009(3) 0.73171(8) 0.62622(6) 0.04211(19) Uani 1 1 d . . . . .
F002 F 0.36111(3) 0.87321(7) 0.47174(8) 0.0453(2) Uani 1 1 d . . . . .
N003 N 0.29464(4) 0.68108(9) 0.48603(8) 0.02460(18) Uani 1 1 d . . . . .
N004 N 0.40723(4) 0.65321(9) 0.43562(8) 0.02459(18) Uani 1 1 d . . . . .
C005 C 0.21552(4) 0.52177(10) 0.43000(8) 0.02117(19) Uani 1 1 d . . . . .
C006 C 0.23519(5) 0.32052(10) 0.32341(8) 0.02193(19) Uani 1 1 d . . . . .
C007 C 0.18922(5) 0.62479(10) 0.49630(8) 0.02193(19) Uani 1 1 d . . . . .
C008 C 0.29722(5) 0.36858(10) 0.31763(8) 0.0229(2) Uani 1 1 d . . . . .
H008 H 0.324235 0.316687 0.277239 0.028 Uiso 1 1 calc R U . . .
C009 C 0.19402(4) 0.39998(10) 0.37925(8) 0.02163(19) Uani 1 1 d . . . . .
H009 H 0.151284 0.369716 0.382034 0.026 Uiso 1 1 calc R U . . .
C00A C 0.32126(4) 0.49113(10) 0.36945(8) 0.02236(19) Uani 1 1 d . . . . .
C00B C 0.38679(5) 0.54183(10) 0.37179(9) 0.0234(2) Uani 1 1 d . . . . .
C00C C 0.27971(4) 0.56401(10) 0.42656(8) 0.02184(19) Uani 1 1 d . . . . .
C00D C 0.21087(5) 0.18312(11) 0.27328(9) 0.0256(2) Uani 1 1 d . . . . .
C00E C 0.12928(5) 0.64141(10) 0.53099(8) 0.0242(2) Uani 1 1 d . . . . .
H00E H 0.095676 0.577274 0.508271 0.029 Uiso 1 1 calc R U . . .
C00F C 0.47177(5) 0.69658(11) 0.44271(9) 0.0270(2) Uani 1 1 d . . . . .
C00G C 0.23942(5) 0.71960(11) 0.53022(9) 0.0242(2) Uani 1 1 d . . . . .
C00H C 0.11871(5) 0.75182(11) 0.59881(9) 0.0274(2) Uani 1 1 d . . . . .
C00I C 0.42893(5) 0.47240(12) 0.30946(9) 0.0280(2) Uani 1 1 d . . . . .
H00I H 0.413296 0.396104 0.263554 0.034 Uiso 1 1 calc R U . . .
C00J C 0.51445(5) 0.62646(12) 0.38246(9) 0.0284(2) Uani 1 1 d . . . . .
C00K C 0.49116(5) 0.51316(12) 0.31435(10) 0.0305(2) Uani 1 1 d . . . . .
H00K H 0.518894 0.465753 0.272208 0.037 Uiso 1 1 calc R U . . .
C00L C 0.49620(5) 0.80891(12) 0.51234(11) 0.0337(2) Uani 1 1 d . . . . .
H00L H 0.468615 0.857327 0.554093 0.040 Uiso 1 1 calc R U . . .
C00M C 0.23016(5) 0.82989(12) 0.59900(10) 0.0302(2) Uani 1 1 d . . . . .
H00M H 0.263887 0.893476 0.622803 0.036 Uiso 1 1 calc R U . . .
C00N C 0.60219(5) 0.77833(13) 0.45940(11) 0.0370(3) Uani 1 1 d . . . . .
H00N H 0.645965 0.806925 0.465338 0.044 Uiso 1 1 calc R U . . .
C00O C 0.57990(5) 0.66950(14) 0.39253(10) 0.0347(3) Uani 1 1 d . . . . .
H00O H 0.608472 0.621929 0.352223 0.042 Uiso 1 1 calc R U . . .
C00P C 0.55992(6) 0.84778(13) 0.51941(12) 0.0368(3) Uani 1 1 d . . . . .
H00P H 0.575666 0.923460 0.566046 0.044 Uiso 1 1 calc R U . . .
C00Q C 0.16990(6) 0.84397(12) 0.63177(10) 0.0312(2) Uani 1 1 d . . . . .
H00Q H 0.162928 0.919156 0.678499 0.037 Uiso 1 1 calc R U . . .
C00R C 0.05318(6) 0.77007(13) 0.63817(11) 0.0356(3) Uani 1 1 d . . . . .
C00S C 0.15070(6) 0.20421(13) 0.17776(11) 0.0353(3) Uani 1 1 d . . . . .
H00A H 0.116473 0.248199 0.211517 0.053 Uiso 1 1 calc R U . . .
H00B H 0.135071 0.116715 0.145050 0.053 Uiso 1 1 calc R U . . .
H00C H 0.162186 0.261157 0.115811 0.053 Uiso 1 1 calc R U . . .
C00T C 0.26225(6) 0.10731(13) 0.22011(11) 0.0353(3) Uani 1 1 d . . . . .
H00D H 0.273103 0.159420 0.154770 0.053 Uiso 1 1 calc R U . . .
H00F H 0.245164 0.019012 0.191943 0.053 Uiso 1 1 calc R U . . .
H00G H 0.301363 0.095019 0.279594 0.053 Uiso 1 1 calc R U . . .
C00U C 0.19299(7) 0.09496(12) 0.37086(11) 0.0378(3) Uani 1 1 d . . . . .
H00H H 0.231100 0.084022 0.432777 0.057 Uiso 1 1 calc R U . . .
H00J H 0.178487 0.006339 0.339208 0.057 Uiso 1 1 calc R U . . .
H00R H 0.157971 0.138149 0.402978 0.057 Uiso 1 1 calc R U . . .
B00V B 0.36182(6) 0.74059(13) 0.50888(12) 0.0297(3) Uani 1 1 d . . . . .
C00W C -0.00192(10) 0.7505(5) 0.5433(2) 0.0517(11) Uani 0.669(8) 1 d . . P A 1
H00S H -0.000369 0.817820 0.482268 0.078 Uiso 0.669(8) 1 calc R U P A 1
H00T H -0.042463 0.760667 0.573328 0.078 Uiso 0.669(8) 1 calc R U P A 1
H00U H 0.000053 0.659912 0.510561 0.078 Uiso 0.669(8) 1 calc R U P A 1
C00X C 0.04808(10) 0.9054(2) 0.7027(2) 0.0472(6) Uani 0.647(4) 1 d . . P A 1
H00V H 0.082049 0.909349 0.772599 0.071 Uiso 0.647(4) 1 calc R U P A 1
H00W H 0.005363 0.911820 0.725539 0.071 Uiso 0.647(4) 1 calc R U P A 1
H00X H 0.053601 0.980629 0.650827 0.071 Uiso 0.647(4) 1 calc R U P A 1
C00Y C 0.05056(14) 0.6601(3) 0.7359(2) 0.0638(10) Uani 0.665(5) 1 d . . P A 1
H00Y H 0.053548 0.569953 0.702926 0.096 Uiso 0.665(5) 1 calc R U P A 1
H H 0.009536 0.668499 0.764646 0.096 Uiso 0.665(5) 1 calc R U P A 1
HA H 0.086961 0.673937 0.800648 0.096 Uiso 0.665(5) 1 calc R U P A 1
C1 C 0.0002(2) 0.6634(8) 0.5754(6) 0.0472(18) Uani 0.331(8) 1 d . . P A 2
H1A H -0.003626 0.670753 0.490537 0.071 Uiso 0.331(8) 1 calc R U P A 2
H1B H -0.041933 0.682626 0.597204 0.071 Uiso 0.331(8) 1 calc R U P A 2
H1C H 0.013941 0.571900 0.600292 0.071 Uiso 0.331(8) 1 calc R U P A 2
C00Z C 0.05646(19) 0.7730(6) 0.7582(3) 0.0449(15) Uani 0.335(5) 1 d . . P A 2
H00Z H 0.071332 0.685243 0.791348 0.067 Uiso 0.335(5) 1 calc R U P A 2
HB H 0.013343 0.792584 0.775593 0.067 Uiso 0.335(5) 1 calc R U P A 2
HC H 0.087021 0.843179 0.792288 0.067 Uiso 0.335(5) 1 calc R U P A 2
C2 C 0.0259(2) 0.9106(5) 0.5773(4) 0.0522(13) Uani 0.353(4) 1 d . . P A 2
H2A H 0.054763 0.984541 0.609165 0.078 Uiso 0.353(4) 1 calc R U P A 2
H2B H -0.017822 0.927572 0.593002 0.078 Uiso 0.353(4) 1 calc R U P A 2
H2C H 0.024232 0.904630 0.492791 0.078 Uiso 0.353(4) 1 calc R U P A 2


_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 B00V 1.3906(15) . ?
F002 B00V 1.3840(15) . ?
N003 C00C 1.3594(13) . ?
N003 C00G 1.4009(13) . ?
N003 B00V 1.5042(14) . ?
N004 C00B 1.3570(13) . ?
N004 C00F 1.4063(12) . ?
N004 B00V 1.6361(16) . ?
C005 C007 1.4483(13) . ?
C005 C009 1.3839(13) . ?
C005 C00C 1.4153(13) . ?
C006 C008 1.3966(13) . ?
C006 C009 1.4107(13) . ?
C006 C00D 1.5330(14) . ?
C007 C00E 1.3960(13) . ?
C007 C00G 1.4126(14) . ?
C008 H008 0.9500 . ?
C008 C00A 1.4091(14) . ?
C009 H009 0.9500 . ?
C00A C00B 1.4571(13) . ?
C00A C00C 1.3895(14) . ?
C00B C00I 1.4182(14) . ?
C00D C00S 1.5369(15) . ?
C00D C00T 1.5322(15) . ?
C00D C00U 1.5331(16) . ?
C00E H00E 0.9500 . ?
C00E C00H 1.3913(15) . ?
C00F C00J 1.4148(16) . ?
C00F C00L 1.4181(16) . ?
C00G C00M 1.3902(15) . ?
C00H C00Q 1.4082(16) . ?
C00H C00R 1.5339(15) . ?
C00I H00I 0.9500 . ?
C00I C00K 1.3555(14) . ?
C00J C00K 1.4108(16) . ?
C00J C00O 1.4198(14) . ?
C00K H00K 0.9500 . ?
C00L H00L 0.9500 . ?
C00L C00P 1.3769(15) . ?
C00M H00M 0.9500 . ?
C00M C00Q 1.3897(15) . ?
C00N H00N 0.9500 . ?
C00N C00O 1.3633(19) . ?
C00N C00P 1.4035(19) . ?
C00O H00O 0.9500 . ?
C00P H00P 0.9500 . ?
C00Q H00Q 0.9500 . ?
C00R C00W 1.459(3) . ?
C00R C00X 1.552(2) . ?
C00R C00Y 1.585(3) . ?
C00R C1 1.610(5) . ?
C00R C00Z 1.387(4) . ?
C00R C2 1.621(4) . ?
C00S H00A 0.9800 . ?
C00S H00B 0.9800 . ?
C00S H00C 0.9800 . ?
C00T H00D 0.9800 . ?
C00T H00F 0.9800 . ?
C00T H00G 0.9800 . ?
C00U H00H 0.9800 . ?
C00U H00J 0.9800 . ?
C00U H00R 0.9800 . ?
C00W H00S 0.9800 . ?
C00W H00T 0.9800 . ?
C00W H00U 0.9800 . ?
C00X H00V 0.9800 . ?
C00X H00W 0.9800 . ?
C00X H00X 0.9800 . ?
C00Y H00Y 0.9800 . ?
C00Y H 0.9800 . ?
C00Y HA 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C00Z H00Z 0.9800 . ?
C00Z HB 0.9800 . ?
C00Z HC 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00C N003 C00G 106.93(8) . . ?
C00C N003 B00V 123.16(9) . . ?
C00G N003 B00V 129.45(9) . . ?
C00B N004 C00F 119.06(9) . . ?
C00B N004 B00V 124.17(8) . . ?
C00F N004 B00V 116.75(9) . . ?
C009 C005 C007 135.89(9) . . ?
C009 C005 C00C 118.91(9) . . ?
C00C C005 C007 105.12(8) . . ?
C008 C006 C009 118.85(9) . . ?
C008 C006 C00D 122.21(9) . . ?
C009 C006 C00D 118.93(8) . . ?
C00E C007 C005 133.32(9) . . ?
C00E C007 C00G 120.19(9) . . ?
C00G C007 C005 106.46(8) . . ?
C006 C008 H008 118.8 . . ?
C006 C008 C00A 122.49(9) . . ?
C00A C008 H008 118.8 . . ?
C005 C009 C006 120.40(9) . . ?
C005 C009 H009 119.8 . . ?
C006 C009 H009 119.8 . . ?
C008 C00A C00B 124.61(9) . . ?
C00C C00A C008 116.60(9) . . ?
C00C C00A C00B 118.71(9) . . ?
N004 C00B C00A 119.59(9) . . ?
N004 C00B C00I 120.81(9) . . ?
C00I C00B C00A 119.58(9) . . ?
N003 C00C C005 111.74(9) . . ?
N003 C00C C00A 125.61(9) . . ?
C00A C00C C005 122.65(9) . . ?
C006 C00D C00S 109.09(9) . . ?
C006 C00D C00U 109.49(8) . . ?
C00T C00D C006 112.40(8) . . ?
C00T C00D C00S 108.53(9) . . ?
C00T C00D C00U 107.64(10) . . ?
C00U C00D C00S 109.65(9) . . ?
C007 C00E H00E 120.0 . . ?
C00H C00E C007 120.06(10) . . ?
C00H C00E H00E 120.0 . . ?
N004 C00F C00J 120.45(10) . . ?
N004 C00F C00L 121.17(10) . . ?
C00J C00F C00L 118.36(10) . . ?
N003 C00G C007 109.73(9) . . ?
C00M C00G N003 129.55(10) . . ?
C00M C00G C007 120.72(9) . . ?
C00E C00H C00Q 118.32(10) . . ?
C00E C00H C00R 120.34(10) . . ?
C00Q C00H C00R 121.32(10) . . ?
C00B C00I H00I 119.5 . . ?
C00K C00I C00B 121.05(10) . . ?
C00K C00I H00I 119.5 . . ?
C00F C00J C00O 119.87(11) . . ?
C00K C00J C00F 119.04(9) . . ?
C00K C00J C00O 121.09(11) . . ?
C00I C00K C00J 119.55(10) . . ?
C00I C00K H00K 120.2 . . ?
C00J C00K H00K 120.2 . . ?
C00F C00L H00L 120.0 . . ?
C00P C00L C00F 119.99(12) . . ?
C00P C00L H00L 120.0 . . ?
C00G C00M H00M 121.1 . . ?
C00Q C00M C00G 117.74(10) . . ?
C00Q C00M H00M 121.1 . . ?
C00O C00N H00N 120.3 . . ?
C00O C00N C00P 119.45(10) . . ?
C00P C00N H00N 120.3 . . ?
C00J C00O H00O 119.6 . . ?
C00N C00O C00J 120.72(12) . . ?
C00N C00O H00O 119.6 . . ?
C00L C00P C00N 121.61(12) . . ?
C00L C00P H00P 119.2 . . ?
C00N C00P H00P 119.2 . . ?
C00H C00Q H00Q 118.5 . . ?
C00M C00Q C00H 122.96(10) . . ?
C00M C00Q H00Q 118.5 . . ?
C00H C00R C00X 112.99(12) . . ?
C00H C00R C00Y 106.42(12) . . ?
C00H C00R C1 111.53(17) . . ?
C00H C00R C2 103.55(17) . . ?
C00W C00R C00H 112.68(12) . . ?
C00W C00R C00X 111.6(2) . . ?
C00W C00R C00Y 109.1(3) . . ?
C00X C00R C00Y 103.46(17) . . ?
C1 C00R C2 102.0(4) . . ?
C00Z C00R C00H 114.80(19) . . ?
C00Z C00R C1 112.1(3) . . ?
C00Z C00R C2 111.9(3) . . ?
C00D C00S H00A 109.5 . . ?
C00D C00S H00B 109.5 . . ?
C00D C00S H00C 109.5 . . ?
H00A C00S H00B 109.5 . . ?
H00A C00S H00C 109.5 . . ?
H00B C00S H00C 109.5 . . ?
C00D C00T H00D 109.5 . . ?
C00D C00T H00F 109.5 . . ?
C00D C00T H00G 109.5 . . ?
H00D C00T H00F 109.5 . . ?
H00D C00T H00G 109.5 . . ?
H00F C00T H00G 109.5 . . ?
C00D C00U H00H 109.5 . . ?
C00D C00U H00J 109.5 . . ?
C00D C00U H00R 109.5 . . ?
H00H C00U H00J 109.5 . . ?
H00H C00U H00R 109.5 . . ?
H00J C00U H00R 109.5 . . ?
F001 B00V N003 111.55(10) . . ?
F001 B00V N004 107.14(9) . . ?
F002 B00V F001 110.24(10) . . ?
F002 B00V N003 111.16(10) . . ?
F002 B00V N004 108.36(9) . . ?
N003 B00V N004 108.23(9) . . ?
C00R C00W H00S 109.5 . . ?
C00R C00W H00T 109.5 . . ?
C00R C00W H00U 109.5 . . ?
H00S C00W H00T 109.5 . . ?
H00S C00W H00U 109.5 . . ?
H00T C00W H00U 109.5 . . ?
C00R C00X H00V 109.5 . . ?
C00R C00X H00W 109.5 . . ?
C00R C00X H00X 109.5 . . ?
H00V C00X H00W 109.5 . . ?
H00V C00X H00X 109.5 . . ?
H00W C00X H00X 109.5 . . ?
C00R C00Y H00Y 109.5 . . ?
C00R C00Y H 109.5 . . ?
C00R C00Y HA 109.5 . . ?
H00Y C00Y H 109.5 . . ?
H00Y C00Y HA 109.5 . . ?
H C00Y HA 109.5 . . ?
C00R C1 H1A 109.5 . . ?
C00R C1 H1B 109.5 . . ?
C00R C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C00R C00Z H00Z 109.5 . . ?
C00R C00Z HB 109.5 . . ?
C00R C00Z HC 109.5 . . ?
H00Z C00Z HB 109.5 . . ?
H00Z C00Z HC 109.5 . . ?
HB C00Z HC 109.5 . . ?
C00R C2 H2A 109.5 . . ?
C00R C2 H2B 109.5 . . ?
C00R C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?

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
N003 C00G C00M C00Q -179.55(10) . . . . ?
N004 C00B C00I C00K 1.74(16) . . . . ?
N004 C00F C00J C00K 0.56(15) . . . . ?
N004 C00F C00J C00O -178.56(9) . . . . ?
N004 C00F C00L C00P 178.83(10) . . . . ?
C005 C007 C00E C00H 178.08(10) . . . . ?
C005 C007 C00G N003 1.16(11) . . . . ?
C005 C007 C00G C00M -177.91(10) . . . . ?
C006 C008 C00A C00B 176.25(9) . . . . ?
C006 C008 C00A C00C -0.60(14) . . . . ?
C007 C005 C009 C006 -177.27(10) . . . . ?
C007 C005 C00C N003 1.03(11) . . . . ?
C007 C005 C00C C00A -179.62(9) . . . . ?
C007 C00E C00H C00Q -0.64(15) . . . . ?
C007 C00E C00H C00R -179.45(10) . . . . ?
C007 C00G C00M C00Q -0.68(16) . . . . ?
C008 C006 C009 C005 -1.67(14) . . . . ?
C008 C006 C00D C00S -119.37(10) . . . . ?
C008 C006 C00D C00T 1.06(14) . . . . ?
C008 C006 C00D C00U 120.63(11) . . . . ?
C008 C00A C00B N004 -172.41(9) . . . . ?
C008 C00A C00B C00I 6.17(15) . . . . ?
C008 C00A C00C N003 177.01(9) . . . . ?
C008 C00A C00C C005 -2.25(14) . . . . ?
C009 C005 C007 C00E -2.74(19) . . . . ?
C009 C005 C007 C00G 175.31(11) . . . . ?
C009 C005 C00C N003 -176.27(8) . . . . ?
C009 C005 C00C C00A 3.08(15) . . . . ?
C009 C006 C008 C00A 2.54(15) . . . . ?
C009 C006 C00D C00S 61.89(12) . . . . ?
C009 C006 C00D C00T -177.69(9) . . . . ?
C009 C006 C00D C00U -58.12(12) . . . . ?
C00A C00B C00I C00K -176.81(10) . . . . ?
C00B N004 C00F C00J 1.11(14) . . . . ?
C00B N004 C00F C00L -177.26(10) . . . . ?
C00B N004 B00V F001 116.88(10) . . . . ?
C00B N004 B00V F002 -124.18(10) . . . . ?
C00B N004 B00V N003 -3.54(14) . . . . ?
C00B C00A C00C N003 -0.03(15) . . . . ?
C00B C00A C00C C005 -179.30(9) . . . . ?
C00B C00I C00K C00J -0.02(17) . . . . ?
C00C N003 C00G C007 -0.54(11) . . . . ?
C00C N003 C00G C00M 178.43(11) . . . . ?
C00C N003 B00V F001 -109.79(11) . . . . ?
C00C N003 B00V F002 126.72(11) . . . . ?
C00C N003 B00V N004 7.83(14) . . . . ?
C00C C005 C007 C00E -179.35(10) . . . . ?
C00C C005 C007 C00G -1.29(10) . . . . ?
C00C C005 C009 C006 -1.02(14) . . . . ?
C00C C00A C00B N004 4.39(14) . . . . ?
C00C C00A C00B C00I -177.04(9) . . . . ?
C00D C006 C008 C00A -176.21(9) . . . . ?
C00D C006 C009 C005 177.12(9) . . . . ?
C00E C007 C00G N003 179.52(9) . . . . ?
C00E C007 C00G C00M 0.45(15) . . . . ?
C00E C00H C00Q C00M 0.40(17) . . . . ?
C00E C00H C00R C00W -46.9(3) . . . . ?
C00E C00H C00R C00X -174.47(13) . . . . ?
C00E C00H C00R C00Y 72.65(18) . . . . ?
C00E C00H C00R C1 -8.8(4) . . . . ?
C00E C00H C00R C00Z 120.1(3) . . . . ?
C00E C00H C00R C2 -117.7(2) . . . . ?
C00F N004 C00B C00A 176.31(9) . . . . ?
C00F N004 C00B C00I -2.24(14) . . . . ?
C00F N004 B00V F001 -61.68(12) . . . . ?
C00F N004 B00V F002 57.26(12) . . . . ?
C00F N004 B00V N003 177.91(9) . . . . ?
C00F C00J C00K C00I -1.08(16) . . . . ?
C00F C00J C00O C00N -0.28(16) . . . . ?
C00F C00L C00P C00N -0.30(18) . . . . ?
C00G N003 C00C C005 -0.33(11) . . . . ?
C00G N003 C00C C00A -179.66(9) . . . . ?
C00G N003 B00V F001 61.36(15) . . . . ?
C00G N003 B00V F002 -62.12(15) . . . . ?
C00G N003 B00V N004 178.99(9) . . . . ?
C00G C007 C00E C00H 0.24(15) . . . . ?
C00G C00M C00Q C00H 0.26(17) . . . . ?
C00J C00F C00L C00P 0.42(17) . . . . ?
C00K C00J C00O C00N -179.38(11) . . . . ?
C00L C00F C00J C00K 178.97(10) . . . . ?
C00L C00F C00J C00O -0.14(16) . . . . ?
C00O C00J C00K C00I 178.02(10) . . . . ?
C00O C00N C00P C00L -0.13(18) . . . . ?
C00P C00N C00O C00J 0.41(17) . . . . ?
C00Q C00H C00R C00W 134.4(2) . . . . ?
C00Q C00H C00R C00X 6.75(18) . . . . ?
C00Q C00H C00R C00Y -106.12(18) . . . . ?
C00Q C00H C00R C1 172.4(4) . . . . ?
C00Q C00H C00R C00Z -58.7(3) . . . . ?
C00Q C00H C00R C2 63.5(2) . . . . ?
C00R C00H C00Q C00M 179.20(11) . . . . ?
B00V N003 C00C C005 172.54(10) . . . . ?
B00V N003 C00C C00A -6.79(16) . . . . ?
B00V N003 C00G C007 -172.80(10) . . . . ?
B00V N003 C00G C00M 6.16(19) . . . . ?
B00V N004 C00B C00A -2.21(15) . . . . ?
B00V N004 C00B C00I 179.23(10) . . . . ?
B00V N004 C00F C00J 179.74(9) . . . . ?
B00V N004 C00F C00L 1.37(14) . . . . ?

_olex2_submission_original_sample_id 20180518_carbazoleBF2_2quinoline
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.747
_oxdiff_exptl_absorpt_empirical_full_min 0.590
####################################################################### 
# 
# 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_fullconjugate_2_autored
_database_code_depnum_ccdc_archive 'CCDC 2254254'
_audit_update_record             
;
2023-04-05 deposited with the CCDC.	2023-06-14 downloaded from the CCDC.
;
_audit_creation_date             2023-04-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
yamakou@shujitsu.ac.jp
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H13 B F2 N2'
_chemical_formula_sum            'C20 H13 B F2 N2'
_chemical_formula_weight         330.13
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H13 B F2 N2'
_chemical_oxdiff_usercomment     'Recryst. from CH2Cl2-Bu2O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.4073(2)
_cell_length_b                   12.8859(3)
_cell_length_c                   15.5809(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.475(2)
_cell_angle_gamma                90
_cell_volume                     1480.41(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    20003
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.9560
_cell_measurement_theta_min      2.6410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0098
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24291
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.905
_diffrn_reflns_theta_min         2.055
_diffrn_ambient_temperature      120
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00  77.00   0.25    5.00    --  -13.00  55.00 -36.00  720
  2  ω   -103.00  77.00   0.25    5.00    --  -13.00  55.00 108.00  720
  3  ω    -68.25  30.00   0.25    5.00    --  -13.00  55.00-108.00  393
  4  ω    -90.00 -29.00   0.25    5.00    --  -13.00  55.00  36.00  244
  5  ω    -99.00  -8.00   0.25    5.00    --  -13.00  27.00-180.00  364
  6  ω   -103.00 -38.00   0.25    5.00    --  -13.00  55.00-180.00  260
;
_diffrn_measurement_device       'AFC11 (Right): Eulerian 3 circle'
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0391451000
_diffrn_orient_matrix_UB_12      0.0471536000
_diffrn_orient_matrix_UB_13      0.0162772000
_diffrn_orient_matrix_UB_21      -0.0260528000
_diffrn_orient_matrix_UB_22      0.0245670000
_diffrn_orient_matrix_UB_23      -0.0400015000
_diffrn_orient_matrix_UB_31      -0.0839015000
_diffrn_orient_matrix_UB_32      0.0143943000
_diffrn_orient_matrix_UB_33      0.0149796000
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3667
_reflns_number_total             3939
_reflns_odcompleteness_completeness 92.12
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.84
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3939
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0749P)²+0.4532P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1219
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N)
2.b Idealised Me refined as rotating group:
 C00O(H00A,H00B,H00C)
;
_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 0.81897(10) 0.94169(5) 0.56814(5) 0.03485(19) Uani 1 1 d . . . . .
F002 F 0.65766(10) 0.86587(6) 0.45426(5) 0.03469(19) Uani 1 1 d . . . . .
N003 N 0.94363(11) 0.78733(6) 0.50752(5) 0.01943(18) Uani 1 1 d . . . . .
N004 N 0.66871(11) 0.78025(6) 0.59267(5) 0.01900(18) Uani 1 1 d . . . . .
C005 C 0.63231(13) 0.64217(8) 0.68316(6) 0.0196(2) Uani 1 1 d . . . . .
C006 C 0.89777(13) 0.64234(7) 0.59997(6) 0.01843(19) Uani 1 1 d . . . . .
C007 C 0.73763(13) 0.68711(7) 0.62301(6) 0.01835(19) Uani 1 1 d . . . . .
C008 C 1.16499(13) 0.64791(8) 0.51871(6) 0.0213(2) Uani 1 1 d . . . . .
C009 C 1.00261(13) 0.69337(8) 0.54118(6) 0.01889(19) Uani 1 1 d . . . . .
C00A C 0.95321(14) 0.54655(8) 0.63757(6) 0.0208(2) Uani 1 1 d . . . . .
C00B C 0.51248(13) 0.79798(7) 0.63447(6) 0.01892(19) Uani 1 1 d . . . . .
C00C C 0.48560(13) 0.71416(8) 0.69072(6) 0.0197(2) Uani 1 1 d . . . . .
C00D C 0.68940(14) 0.54689(8) 0.72080(7) 0.0230(2) Uani 1 1 d . . . . .
H00D H 0.620790 0.514886 0.761992 0.028 Uiso 1 1 calc R U . . .
C00E C 1.11767(14) 0.50127(8) 0.61312(7) 0.0238(2) Uani 1 1 d . . . . .
H00E H 1.156850 0.436268 0.636880 0.029 Uiso 1 1 calc R U . . .
C00F C 1.04367(14) 0.83655(8) 0.45263(7) 0.0236(2) Uani 1 1 d . . . . .
H00F H 1.002840 0.901686 0.429735 0.028 Uiso 1 1 calc R U . . .
C00G C 0.33394(14) 0.71424(8) 0.73810(6) 0.0221(2) Uani 1 1 d . . . . .
H00G H 0.314513 0.658420 0.775970 0.027 Uiso 1 1 calc R U . . .
C00H C 0.39211(14) 0.88137(8) 0.62517(7) 0.0225(2) Uani 1 1 d . . . . .
H00H H 0.410984 0.937565 0.587576 0.027 Uiso 1 1 calc R U . . .
C00I C 0.84570(14) 0.49995(8) 0.69764(7) 0.0237(2) Uani 1 1 d . . . . .
H00I H 0.881830 0.435015 0.722548 0.028 Uiso 1 1 calc R U . . .
C00J C 0.24362(14) 0.87881(9) 0.67314(7) 0.0247(2) Uani 1 1 d . . . . .
H00J H 0.159760 0.934748 0.667932 0.030 Uiso 1 1 calc R U . . .
C00K C 1.21828(14) 0.54956(8) 0.55668(7) 0.0247(2) Uani 1 1 d . . . . .
H00K H 1.326650 0.517589 0.541883 0.030 Uiso 1 1 calc R U . . .
C00L C 0.21256(14) 0.79622(9) 0.72935(7) 0.0236(2) Uani 1 1 d . . . . .
C00M C 1.26495(15) 0.70151(9) 0.46101(7) 0.0264(2) Uani 1 1 d . . . . .
H00M H 1.374625 0.672811 0.444527 0.032 Uiso 1 1 calc R U . . .
C00N C 1.20425(15) 0.79592(9) 0.42811(7) 0.0276(2) Uani 1 1 d . . . . .
H00N H 1.271729 0.832716 0.389077 0.033 Uiso 1 1 calc R U . . .
C00O C 0.04813(15) 0.79776(10) 0.77967(8) 0.0312(3) Uani 1 1 d . . . . .
H00A H 0.037687 0.731010 0.808933 0.047 Uiso 1 1 calc R U . . .
H00B H -0.060933 0.809725 0.740169 0.047 Uiso 1 1 calc R U . . .
H00C H 0.060939 0.853547 0.822572 0.047 Uiso 1 1 calc R U . . .
B00P B 0.76283(15) 0.84764(9) 0.53085(8) 0.0214(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 B00P 1.3904(13) . ?
F002 B00P 1.3816(13) . ?
N003 C009 1.3741(13) . ?
N003 C00F 1.3431(12) . ?
N003 B00P 1.6194(14) . ?
N004 C007 1.3705(12) . ?
N004 C00B 1.3998(12) . ?
N004 B00P 1.5152(13) . ?
C005 C007 1.4007(13) . ?
C005 C00C 1.4421(14) . ?
C005 C00D 1.4082(13) . ?
C006 C007 1.3964(13) . ?
C006 C009 1.4179(13) . ?
C006 C00A 1.4105(13) . ?
C008 C009 1.4117(13) . ?
C008 C00K 1.4379(15) . ?
C008 C00M 1.4001(15) . ?
C00A C00E 1.4346(14) . ?
C00A C00I 1.4188(14) . ?
C00B C00C 1.4170(13) . ?
C00B C00H 1.3951(14) . ?
C00C C00G 1.4018(13) . ?
C00D H00D 0.9500 . ?
C00D C00I 1.3843(15) . ?
C00E H00E 0.9500 . ?
C00E C00K 1.3568(15) . ?
C00F H00F 0.9500 . ?
C00F C00N 1.3862(15) . ?
C00G H00G 0.9500 . ?
C00G C00L 1.3855(15) . ?
C00H H00H 0.9500 . ?
C00H C00J 1.3879(14) . ?
C00I H00I 0.9500 . ?
C00J H00J 0.9500 . ?
C00J C00L 1.4110(16) . ?
C00K H00K 0.9500 . ?
C00L C00O 1.5103(14) . ?
C00M H00M 0.9500 . ?
C00M C00N 1.3788(17) . ?
C00N H00N 0.9500 . ?
C00O H00A 0.9800 . ?
C00O H00B 0.9800 . ?
C00O H00C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C009 N003 B00P 125.23(8) . . ?
C00F N003 C009 118.98(9) . . ?
C00F N003 B00P 115.77(8) . . ?
C007 N004 C00B 106.24(8) . . ?
C007 N004 B00P 122.84(8) . . ?
C00B N004 B00P 130.78(8) . . ?
C007 C005 C00C 105.12(8) . . ?
C007 C005 C00D 118.35(9) . . ?
C00D C005 C00C 136.51(9) . . ?
C007 C006 C009 120.37(9) . . ?
C007 C006 C00A 118.40(9) . . ?
C00A C006 C009 121.23(9) . . ?
N004 C007 C005 112.33(8) . . ?
N004 C007 C006 124.80(9) . . ?
C006 C007 C005 122.83(9) . . ?
C009 C008 C00K 118.08(9) . . ?
C00M C008 C009 118.03(10) . . ?
C00M C008 C00K 123.90(10) . . ?
N003 C009 C006 118.77(9) . . ?
N003 C009 C008 121.23(9) . . ?
C008 C009 C006 120.00(9) . . ?
C006 C00A C00E 117.81(9) . . ?
C006 C00A C00I 119.00(9) . . ?
C00I C00A C00E 123.18(9) . . ?
N004 C00B C00C 109.55(8) . . ?
C00H C00B N004 128.75(9) . . ?
C00H C00B C00C 121.69(9) . . ?
C00B C00C C005 106.75(8) . . ?
C00G C00C C005 133.75(9) . . ?
C00G C00C C00B 119.48(9) . . ?
C005 C00D H00D 120.1 . . ?
C00I C00D C005 119.85(9) . . ?
C00I C00D H00D 120.1 . . ?
C00A C00E H00E 119.4 . . ?
C00K C00E C00A 121.23(10) . . ?
C00K C00E H00E 119.4 . . ?
N003 C00F H00F 118.8 . . ?
N003 C00F C00N 122.49(10) . . ?
C00N C00F H00F 118.8 . . ?
C00C C00G H00G 120.2 . . ?
C00L C00G C00C 119.60(10) . . ?
C00L C00G H00G 120.2 . . ?
C00B C00H H00H 121.4 . . ?
C00J C00H C00B 117.20(9) . . ?
C00J C00H H00H 121.4 . . ?
C00A C00I H00I 119.2 . . ?
C00D C00I C00A 121.54(9) . . ?
C00D C00I H00I 119.2 . . ?
C00H C00J H00J 118.8 . . ?
C00H C00J C00L 122.46(10) . . ?
C00L C00J H00J 118.8 . . ?
C008 C00K H00K 119.2 . . ?
C00E C00K C008 121.65(9) . . ?
C00E C00K H00K 119.2 . . ?
C00G C00L C00J 119.56(10) . . ?
C00G C00L C00O 120.46(10) . . ?
C00J C00L C00O 119.98(10) . . ?
C008 C00M H00M 120.0 . . ?
C00N C00M C008 120.02(10) . . ?
C00N C00M H00M 120.0 . . ?
C00F C00N H00N 120.4 . . ?
C00M C00N C00F 119.26(10) . . ?
C00M C00N H00N 120.4 . . ?
C00L C00O H00A 109.5 . . ?
C00L C00O H00B 109.5 . . ?
C00L C00O H00C 109.5 . . ?
H00A C00O H00B 109.5 . . ?
H00A C00O H00C 109.5 . . ?
H00B C00O H00C 109.5 . . ?
F001 B00P N003 106.93(8) . . ?
F001 B00P N004 111.80(9) . . ?
F002 B00P F001 109.53(9) . . ?
F002 B00P N003 107.33(8) . . ?
F002 B00P N004 113.00(9) . . ?
N004 B00P N003 107.95(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N003 C00F C00N C00M -0.08(17) . . . . ?
N004 C00B C00C C005 0.20(11) . . . . ?
N004 C00B C00C C00G -178.55(8) . . . . ?
N004 C00B C00H C00J 178.37(10) . . . . ?
C005 C00C C00G C00L -178.39(10) . . . . ?
C005 C00D C00I C00A 1.21(16) . . . . ?
C006 C00A C00E C00K 0.97(15) . . . . ?
C006 C00A C00I C00D -0.78(16) . . . . ?
C007 N004 C00B C00C -0.28(10) . . . . ?
C007 N004 C00B C00H -179.08(10) . . . . ?
C007 N004 B00P F001 -115.11(10) . . . . ?
C007 N004 B00P F002 120.77(10) . . . . ?
C007 N004 B00P N003 2.24(13) . . . . ?
C007 C005 C00C C00B -0.04(10) . . . . ?
C007 C005 C00C C00G 178.45(10) . . . . ?
C007 C005 C00D C00I -0.31(15) . . . . ?
C007 C006 C009 N003 0.00(14) . . . . ?
C007 C006 C009 C008 179.55(8) . . . . ?
C007 C006 C00A C00E 179.80(9) . . . . ?
C007 C006 C00A C00I -0.55(14) . . . . ?
C008 C00M C00N C00F -0.19(16) . . . . ?
C009 N003 C00F C00N 0.35(16) . . . . ?
C009 N003 B00P F001 118.18(10) . . . . ?
C009 N003 B00P F002 -124.37(10) . . . . ?
C009 N003 B00P N004 -2.27(13) . . . . ?
C009 C006 C007 N004 0.04(15) . . . . ?
C009 C006 C007 C005 -177.54(9) . . . . ?
C009 C006 C00A C00E -1.18(14) . . . . ?
C009 C006 C00A C00I 178.47(9) . . . . ?
C009 C008 C00K C00E -0.53(15) . . . . ?
C009 C008 C00M C00N 0.18(16) . . . . ?
C00A C006 C007 N004 179.06(9) . . . . ?
C00A C006 C007 C005 1.49(15) . . . . ?
C00A C006 C009 N003 -178.99(8) . . . . ?
C00A C006 C009 C008 0.56(15) . . . . ?
C00A C00E C00K C008 -0.12(16) . . . . ?
C00B N004 C007 C005 0.26(11) . . . . ?
C00B N004 C007 C006 -177.54(9) . . . . ?
C00B N004 B00P F001 59.99(14) . . . . ?
C00B N004 B00P F002 -64.13(14) . . . . ?
C00B N004 B00P N003 177.33(9) . . . . ?
C00B C00C C00G C00L -0.05(14) . . . . ?
C00B C00H C00J C00L -0.04(15) . . . . ?
C00C C005 C007 N004 -0.14(11) . . . . ?
C00C C005 C007 C006 177.71(9) . . . . ?
C00C C005 C00D C00I -178.58(11) . . . . ?
C00C C00B C00H C00J -0.30(14) . . . . ?
C00C C00G C00L C00J -0.28(15) . . . . ?
C00C C00G C00L C00O 179.90(9) . . . . ?
C00D C005 C007 N004 -178.91(8) . . . . ?
C00D C005 C007 C006 -1.06(15) . . . . ?
C00D C005 C00C C00B 178.39(11) . . . . ?
C00D C005 C00C C00G -3.1(2) . . . . ?
C00E C00A C00I C00D 178.85(9) . . . . ?
C00F N003 C009 C006 179.19(9) . . . . ?
C00F N003 C009 C008 -0.36(14) . . . . ?
C00F N003 B00P F001 -59.80(11) . . . . ?
C00F N003 B00P F002 57.66(11) . . . . ?
C00F N003 B00P N004 179.76(8) . . . . ?
C00H C00B C00C C005 179.10(9) . . . . ?
C00H C00B C00C C00G 0.35(14) . . . . ?
C00H C00J C00L C00G 0.33(16) . . . . ?
C00H C00J C00L C00O -179.84(10) . . . . ?
C00I C00A C00E C00K -178.67(10) . . . . ?
C00K C008 C009 N003 179.85(9) . . . . ?
C00K C008 C009 C006 0.31(14) . . . . ?
C00K C008 C00M C00N -179.56(10) . . . . ?
C00M C008 C009 N003 0.10(15) . . . . ?
C00M C008 C009 C006 -179.44(9) . . . . ?
C00M C008 C00K C00E 179.20(10) . . . . ?
B00P N003 C009 C006 1.27(14) . . . . ?
B00P N003 C009 C008 -178.28(9) . . . . ?
B00P N003 C00F C00N 178.46(9) . . . . ?
B00P N004 C007 C005 176.40(9) . . . . ?
B00P N004 C007 C006 -1.40(15) . . . . ?
B00P N004 C00B C00C -175.99(10) . . . . ?
B00P N004 C00B C00H 5.21(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.354
_oxdiff_exptl_absorpt_empirical_full_min 0.528
####################################################################### 
# 
# 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_190120_yamakou__autored
_database_code_depnum_ccdc_archive 'CCDC 2254262'
_audit_update_record             
;
2023-04-05 deposited with the CCDC.	2023-06-14 downloaded from the CCDC.
;
_audit_creation_date             2023-04-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
yamakou@shujitsu.ac.jp
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H26 B F2 N3'
_chemical_formula_sum            'C24 H26 B F2 N3'
_chemical_formula_weight         405.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H26 B F2 N3'
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'
N N 0.0061 0.0033 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.1855(3)
_cell_length_b                   11.2431(2)
_cell_length_c                   11.9494(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.172(2)
_cell_angle_gamma                90
_cell_volume                     2053.89(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    26854
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.0050
_cell_measurement_theta_min      2.6020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71045
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_unetI/netI     0.0082
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            33705
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.904
_diffrn_reflns_theta_min         2.665
_diffrn_ambient_temperature      120
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00  77.00   0.25    5.00    --  -13.00  55.00 -36.00  720
  2  ω   -103.00  77.00   0.25    5.00    --  -13.00  55.00 108.00  720
  3  ω    -86.25  52.00   0.25    5.00    --  -13.00  55.00-108.00  553
  4  ω    -53.00   8.00   0.25    5.00    --  -13.00   0.00-180.00  244
  5  ω   -103.00  11.00   0.25    5.00    --  -13.00  55.00  36.00  456
;
_diffrn_measurement_device       'AFC11 (Right): Eulerian 3 circle'
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0124232000
_diffrn_orient_matrix_UB_12      0.0150581000
_diffrn_orient_matrix_UB_13      -0.0499009000
_diffrn_orient_matrix_UB_21      -0.0446904000
_diffrn_orient_matrix_UB_22      0.0022449000
_diffrn_orient_matrix_UB_23      -0.0357398000
_diffrn_orient_matrix_UB_31      -0.0014278000
_diffrn_orient_matrix_UB_32      0.0611937000
_diffrn_orient_matrix_UB_33      0.0135538000
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5150
_reflns_number_total             5480
_reflns_odcompleteness_completeness 92.27
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.84
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         5480
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.045
_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)+(0.0595P)²+0.7296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1110
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00E(H00E), C00G(H00G), C00I(H00I), C00K(H00K),
 C00M(H00M), C00N(H00N)
2.b Idealised Me refined as rotating group:
 C00L(H00A,H00C,H00D), C00P(H00F,H00H,H00J), C00Q(H00L,H00O,H00P), C00R(H00Q,
 H00R,H00S), C00S(H00T,H00U,H00V), C00T(H00W,H00X,H00Y)
;
_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 0.35010(4) 0.38411(6) 0.14402(5) 0.02957(15) Uani 1 1 d . . . . .
F002 F 0.42480(4) 0.55265(6) 0.21692(6) 0.02903(15) Uani 1 1 d . . . . .
N003 N 0.44929(5) 0.38227(7) 0.34777(7) 0.01818(16) Uani 1 1 d . . . . .
N004 N 0.30845(5) 0.49616(7) 0.28968(7) 0.01907(16) Uani 1 1 d . . . . .
N005 N 0.51465(6) 0.34187(7) 0.31009(7) 0.02112(17) Uani 1 1 d . . . . .
C006 C 0.30019(6) 0.46529(8) 0.63234(8) 0.01792(17) Uani 1 1 d . . . . .
C007 C 0.37631(6) 0.41527(8) 0.49101(8) 0.01734(17) Uani 1 1 d . . . . .
C008 C 0.31206(6) 0.47875(8) 0.40456(8) 0.01749(17) Uani 1 1 d . . . . .
C009 C 0.36844(6) 0.40879(8) 0.60432(8) 0.01854(18) Uani 1 1 d . . . . .
H009 H 0.410639 0.364731 0.664167 0.022 Uiso 1 1 calc R U . . .
C00A C 0.29521(6) 0.45455(9) 0.75823(8) 0.02030(18) Uani 1 1 d . . . . .
C00B C 0.23683(6) 0.52800(8) 0.54316(8) 0.01847(18) Uani 1 1 d . . . . .
H00B H 0.190190 0.566337 0.560605 0.022 Uiso 1 1 calc R U . . .
C00C C 0.24186(6) 0.53444(8) 0.42901(8) 0.01774(17) Uani 1 1 d . . . . .
C00D C 0.23323(6) 0.56362(9) 0.23573(8) 0.01962(18) Uani 1 1 d . . . . .
C00E C 0.11107(6) 0.65164(9) 0.28291(8) 0.02052(19) Uani 1 1 d . . . . .
H00E H 0.082423 0.668615 0.338883 0.025 Uiso 1 1 calc R U . . .
C00F C 0.44780(6) 0.36388(8) 0.45895(8) 0.01781(17) Uani 1 1 d . . . . .
C00G C 0.58011(6) 0.28561(8) 0.38655(9) 0.02183(19) Uani 1 1 d . . . . .
H00G H 0.627326 0.260495 0.361586 0.026 Uiso 1 1 calc R U . . .
C00H C 0.07425(6) 0.68935(9) 0.16601(8) 0.02158(19) Uani 1 1 d . . . . .
C00I C 0.19827(7) 0.60207(9) 0.11849(9) 0.0234(2) Uani 1 1 d . . . . .
H00I H 0.227432 0.586693 0.062762 0.028 Uiso 1 1 calc R U . . .
C00J C 0.18999(6) 0.58893(9) 0.31820(8) 0.01918(18) Uani 1 1 d . . . . .
C00K C 0.51631(7) 0.29794(9) 0.53905(9) 0.02231(19) Uani 1 1 d . . . . .
H00K H 0.515276 0.279952 0.616260 0.027 Uiso 1 1 calc R U . . .
C00L C 0.38647(7) 0.46314(11) 0.85195(9) 0.0284(2) Uani 1 1 d . . . . .
H00A H 0.422254 0.395805 0.843047 0.043 Uiso 1 1 calc R U . . .
H00C H 0.381026 0.461382 0.931230 0.043 Uiso 1 1 calc R U . . .
H00D H 0.414368 0.537726 0.841387 0.043 Uiso 1 1 calc R U . . .
C00M C 0.11961(7) 0.66340(10) 0.08599(9) 0.0244(2) Uani 1 1 d . . . . .
H00M H 0.095028 0.689206 0.006193 0.029 Uiso 1 1 calc R U . . .
C00N C 0.58407(7) 0.26055(9) 0.50338(9) 0.0240(2) Uani 1 1 d . . . . .
H00N H 0.632356 0.218894 0.555974 0.029 Uiso 1 1 calc R U . . .
C00O C -0.01534(6) 0.75077(10) 0.12161(9) 0.0243(2) Uani 1 1 d . . . . .
C00P C 0.23740(8) 0.55192(12) 0.78328(10) 0.0337(3) Uani 1 1 d . . . . .
H00F H 0.257343 0.629931 0.765935 0.051 Uiso 1 1 calc R U . . .
H00H H 0.241289 0.548679 0.866820 0.051 Uiso 1 1 calc R U . . .
H00J H 0.176579 0.539436 0.733123 0.051 Uiso 1 1 calc R U . . .
C00Q C -0.01189(7) 0.86139(11) 0.04829(11) 0.0314(2) Uani 1 1 d . . . . .
H00L H 0.030579 0.918064 0.097688 0.047 Uiso 1 1 calc R U . . .
H00O H -0.069834 0.898559 0.019917 0.047 Uiso 1 1 calc R U . . .
H00P H 0.005803 0.838261 -0.019604 0.047 Uiso 1 1 calc R U . . .
C00R C 0.25565(9) 0.33284(12) 0.76992(11) 0.0357(3) Uani 1 1 d . . . . .
H00Q H 0.196591 0.327169 0.712220 0.054 Uiso 1 1 calc R U . . .
H00R H 0.252804 0.324088 0.850166 0.054 Uiso 1 1 calc R U . . .
H00S H 0.292339 0.269635 0.754824 0.054 Uiso 1 1 calc R U . . .
C00S C -0.04591(8) 0.79213(13) 0.22398(11) 0.0348(3) Uani 1 1 d . . . . .
H00T H -0.053396 0.722906 0.269552 0.052 Uiso 1 1 calc R U . . .
H00U H -0.101767 0.834216 0.192020 0.052 Uiso 1 1 calc R U . . .
H00V H -0.002072 0.845696 0.275748 0.052 Uiso 1 1 calc R U . . .
C00T C -0.08260(8) 0.66257(12) 0.04429(12) 0.0378(3) Uani 1 1 d . . . . .
H00W H -0.064298 0.637216 -0.022461 0.057 Uiso 1 1 calc R U . . .
H00X H -0.139954 0.701196 0.014195 0.057 Uiso 1 1 calc R U . . .
H00Y H -0.086435 0.593063 0.091821 0.057 Uiso 1 1 calc R U . . .
B00U B 0.37973(7) 0.45664(10) 0.24171(9) 0.0205(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 B00U 1.3747(12) . ?
F002 B00U 1.3881(13) . ?
N003 N005 1.3570(11) . ?
N003 C00F 1.3525(12) . ?
N003 B00U 1.6235(13) . ?
N004 C008 1.3688(11) . ?
N004 C00D 1.3991(12) . ?
N004 B00U 1.5137(13) . ?
N005 C00G 1.3120(13) . ?
C006 C009 1.4067(13) . ?
C006 C00A 1.5374(12) . ?
C006 C00B 1.4024(13) . ?
C007 C008 1.3973(12) . ?
C007 C009 1.4028(12) . ?
C007 C00F 1.4527(12) . ?
C008 C00C 1.4095(12) . ?
C009 H009 0.9500 . ?
C00A C00L 1.5359(14) . ?
C00A C00P 1.5323(14) . ?
C00A C00R 1.5364(15) . ?
C00B H00B 0.9500 . ?
C00B C00C 1.3948(12) . ?
C00C C00J 1.4502(12) . ?
C00D C00I 1.3961(13) . ?
C00D C00J 1.4124(13) . ?
C00E H00E 0.9500 . ?
C00E C00H 1.3926(13) . ?
C00E C00J 1.3975(13) . ?
C00F C00K 1.4136(13) . ?
C00G H00G 0.9500 . ?
C00G C00N 1.4049(14) . ?
C00H C00M 1.4141(14) . ?
C00H C00O 1.5348(13) . ?
C00I H00I 0.9500 . ?
C00I C00M 1.3865(14) . ?
C00K H00K 0.9500 . ?
C00K C00N 1.3668(14) . ?
C00L H00A 0.9800 . ?
C00L H00C 0.9800 . ?
C00L H00D 0.9800 . ?
C00M H00M 0.9500 . ?
C00N H00N 0.9500 . ?
C00O C00Q 1.5329(15) . ?
C00O C00S 1.5345(16) . ?
C00O C00T 1.5366(16) . ?
C00P H00F 0.9800 . ?
C00P H00H 0.9800 . ?
C00P H00J 0.9800 . ?
C00Q H00L 0.9800 . ?
C00Q H00O 0.9800 . ?
C00Q H00P 0.9800 . ?
C00R H00Q 0.9800 . ?
C00R H00R 0.9800 . ?
C00R H00S 0.9800 . ?
C00S H00T 0.9800 . ?
C00S H00U 0.9800 . ?
C00S H00V 0.9800 . ?
C00T H00W 0.9800 . ?
C00T H00X 0.9800 . ?
C00T H00Y 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N005 N003 B00U 109.25(7) . . ?
C00F N003 N005 122.83(8) . . ?
C00F N003 B00U 127.88(8) . . ?
C008 N004 C00D 106.48(7) . . ?
C008 N004 B00U 123.43(8) . . ?
C00D N004 B00U 129.84(8) . . ?
C00G N005 N003 118.00(8) . . ?
C009 C006 C00A 119.67(8) . . ?
C00B C006 C009 118.79(8) . . ?
C00B C006 C00A 121.52(8) . . ?
C008 C007 C009 117.30(8) . . ?
C008 C007 C00F 118.16(8) . . ?
C009 C007 C00F 124.51(8) . . ?
N004 C008 C007 126.22(8) . . ?
N004 C008 C00C 111.87(8) . . ?
C007 C008 C00C 121.91(8) . . ?
C006 C009 H009 118.9 . . ?
C007 C009 C006 122.25(8) . . ?
C007 C009 H009 118.9 . . ?
C00L C00A C006 111.20(8) . . ?
C00L C00A C00R 108.63(9) . . ?
C00P C00A C006 111.51(8) . . ?
C00P C00A C00L 108.38(9) . . ?
C00P C00A C00R 108.61(9) . . ?
C00R C00A C006 108.44(8) . . ?
C006 C00B H00B 119.8 . . ?
C00C C00B C006 120.42(8) . . ?
C00C C00B H00B 119.8 . . ?
C008 C00C C00J 105.24(8) . . ?
C00B C00C C008 119.31(8) . . ?
C00B C00C C00J 135.45(9) . . ?
N004 C00D C00J 110.08(8) . . ?
C00I C00D N004 129.41(9) . . ?
C00I C00D C00J 120.49(9) . . ?
C00H C00E H00E 119.9 . . ?
C00H C00E C00J 120.26(9) . . ?
C00J C00E H00E 119.9 . . ?
N003 C00F C007 118.09(8) . . ?
N003 C00F C00K 118.83(8) . . ?
C00K C00F C007 123.07(8) . . ?
N005 C00G H00G 118.3 . . ?
N005 C00G C00N 123.48(9) . . ?
C00N C00G H00G 118.3 . . ?
C00E C00H C00M 117.98(9) . . ?
C00E C00H C00O 121.89(9) . . ?
C00M C00H C00O 120.03(8) . . ?
C00D C00I H00I 121.1 . . ?
C00M C00I C00D 117.86(9) . . ?
C00M C00I H00I 121.1 . . ?
C00D C00J C00C 106.32(8) . . ?
C00E C00J C00C 133.34(9) . . ?
C00E C00J C00D 120.29(8) . . ?
C00F C00K H00K 120.6 . . ?
C00N C00K C00F 118.78(9) . . ?
C00N C00K H00K 120.6 . . ?
C00A C00L H00A 109.5 . . ?
C00A C00L H00C 109.5 . . ?
C00A C00L H00D 109.5 . . ?
H00A C00L H00C 109.5 . . ?
H00A C00L H00D 109.5 . . ?
H00C C00L H00D 109.5 . . ?
C00H C00M H00M 118.4 . . ?
C00I C00M C00H 123.10(9) . . ?
C00I C00M H00M 118.4 . . ?
C00G C00N H00N 121.0 . . ?
C00K C00N C00G 117.95(9) . . ?
C00K C00N H00N 121.0 . . ?
C00H C00O C00T 108.65(9) . . ?
C00Q C00O C00H 110.79(8) . . ?
C00Q C00O C00S 106.95(10) . . ?
C00Q C00O C00T 109.36(9) . . ?
C00S C00O C00H 112.09(8) . . ?
C00S C00O C00T 108.95(10) . . ?
C00A C00P H00F 109.5 . . ?
C00A C00P H00H 109.5 . . ?
C00A C00P H00J 109.5 . . ?
H00F C00P H00H 109.5 . . ?
H00F C00P H00J 109.5 . . ?
H00H C00P H00J 109.5 . . ?
C00O C00Q H00L 109.5 . . ?
C00O C00Q H00O 109.5 . . ?
C00O C00Q H00P 109.5 . . ?
H00L C00Q H00O 109.5 . . ?
H00L C00Q H00P 109.5 . . ?
H00O C00Q H00P 109.5 . . ?
C00A C00R H00Q 109.5 . . ?
C00A C00R H00R 109.5 . . ?
C00A C00R H00S 109.5 . . ?
H00Q C00R H00R 109.5 . . ?
H00Q C00R H00S 109.5 . . ?
H00R C00R H00S 109.5 . . ?
C00O C00S H00T 109.5 . . ?
C00O C00S H00U 109.5 . . ?
C00O C00S H00V 109.5 . . ?
H00T C00S H00U 109.5 . . ?
H00T C00S H00V 109.5 . . ?
H00U C00S H00V 109.5 . . ?
C00O C00T H00W 109.5 . . ?
C00O C00T H00X 109.5 . . ?
C00O C00T H00Y 109.5 . . ?
H00W C00T H00X 109.5 . . ?
H00W C00T H00Y 109.5 . . ?
H00X C00T H00Y 109.5 . . ?
F001 B00U F002 109.96(8) . . ?
F001 B00U N003 108.45(8) . . ?
F001 B00U N004 113.51(9) . . ?
F002 B00U N003 106.79(8) . . ?
F002 B00U N004 111.83(8) . . ?
N004 B00U N003 105.96(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
N003 N005 C00G C00N 2.93(14) . . . . ?
N003 C00F C00K C00N 3.47(14) . . . . ?
N004 C008 C00C C00B -178.39(8) . . . . ?
N004 C008 C00C C00J 1.07(11) . . . . ?
N004 C00D C00I C00M 176.74(10) . . . . ?
N004 C00D C00J C00C 0.30(11) . . . . ?
N004 C00D C00J C00E -177.51(9) . . . . ?
N005 N003 C00F C007 177.59(8) . . . . ?
N005 N003 C00F C00K -1.18(14) . . . . ?
N005 N003 B00U F001 56.67(10) . . . . ?
N005 N003 B00U F002 -61.78(9) . . . . ?
N005 N003 B00U N004 178.86(7) . . . . ?
N005 C00G C00N C00K -0.62(16) . . . . ?
C006 C00B C00C C008 -0.95(14) . . . . ?
C006 C00B C00C C00J 179.79(10) . . . . ?
C007 C008 C00C C00B 1.10(14) . . . . ?
C007 C008 C00C C00J -179.44(8) . . . . ?
C007 C00F C00K C00N -175.23(9) . . . . ?
C008 N004 C00D C00I -177.71(10) . . . . ?
C008 N004 C00D C00J 0.34(11) . . . . ?
C008 N004 B00U F001 124.65(10) . . . . ?
C008 N004 B00U F002 -110.24(10) . . . . ?
C008 N004 B00U N003 5.74(12) . . . . ?
C008 C007 C009 C006 -1.30(14) . . . . ?
C008 C007 C00F N003 1.32(13) . . . . ?
C008 C007 C00F C00K -179.97(9) . . . . ?
C008 C00C C00J C00D -0.81(10) . . . . ?
C008 C00C C00J C00E 176.60(10) . . . . ?
C009 C006 C00A C00L 40.13(12) . . . . ?
C009 C006 C00A C00P 161.23(10) . . . . ?
C009 C006 C00A C00R -79.24(11) . . . . ?
C009 C006 C00B C00C -0.28(14) . . . . ?
C009 C007 C008 N004 179.43(9) . . . . ?
C009 C007 C008 C00C 0.02(14) . . . . ?
C009 C007 C00F N003 -176.67(9) . . . . ?
C009 C007 C00F C00K 2.04(15) . . . . ?
C00A C006 C009 C007 179.91(9) . . . . ?
C00A C006 C00B C00C -178.71(9) . . . . ?
C00B C006 C009 C007 1.45(14) . . . . ?
C00B C006 C00A C00L -141.46(10) . . . . ?
C00B C006 C00A C00P -20.36(13) . . . . ?
C00B C006 C00A C00R 99.17(11) . . . . ?
C00B C00C C00J C00D 178.53(11) . . . . ?
C00B C00C C00J C00E -4.07(19) . . . . ?
C00D N004 C008 C007 179.64(9) . . . . ?
C00D N004 C008 C00C -0.90(11) . . . . ?
C00D N004 B00U F001 -61.74(13) . . . . ?
C00D N004 B00U F002 63.37(13) . . . . ?
C00D N004 B00U N003 179.36(9) . . . . ?
C00D C00I C00M C00H 0.62(16) . . . . ?
C00E C00H C00M C00I 0.31(16) . . . . ?
C00E C00H C00O C00Q 133.75(11) . . . . ?
C00E C00H C00O C00S 14.36(14) . . . . ?
C00E C00H C00O C00T -106.09(12) . . . . ?
C00F N003 N005 C00G -1.99(13) . . . . ?
C00F N003 B00U F001 -125.54(10) . . . . ?
C00F N003 B00U F002 116.00(10) . . . . ?
C00F N003 B00U N004 -3.35(13) . . . . ?
C00F C007 C008 N004 1.30(14) . . . . ?
C00F C007 C008 C00C -178.12(8) . . . . ?
C00F C007 C009 C006 176.70(9) . . . . ?
C00F C00K C00N C00G -2.61(15) . . . . ?
C00H C00E C00J C00C -176.89(10) . . . . ?
C00H C00E C00J C00D 0.22(15) . . . . ?
C00I C00D C00J C00C 178.56(9) . . . . ?
C00I C00D C00J C00E 0.75(15) . . . . ?
C00J C00D C00I C00M -1.14(15) . . . . ?
C00J C00E C00H C00M -0.73(15) . . . . ?
C00J C00E C00H C00O 175.68(9) . . . . ?
C00M C00H C00O C00Q -49.91(13) . . . . ?
C00M C00H C00O C00S -169.30(10) . . . . ?
C00M C00H C00O C00T 70.25(12) . . . . ?
C00O C00H C00M C00I -176.17(10) . . . . ?
B00U N003 N005 C00G 175.93(8) . . . . ?
B00U N003 C00F C007 0.08(14) . . . . ?
B00U N003 C00F C00K -178.69(9) . . . . ?
B00U N004 C008 C007 -5.47(15) . . . . ?
B00U N004 C008 C00C 173.99(8) . . . . ?
B00U N004 C00D C00I 7.84(17) . . . . ?
B00U N004 C00D C00J -174.10(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.647
_oxdiff_exptl_absorpt_empirical_full_min 0.566
####################################################################### 
# 
# 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_190703_yamakou_2_autored
_database_code_depnum_ccdc_archive 'CCDC 2254278'
_audit_update_record             
;
2023-04-05 deposited with the CCDC.	2023-06-14 downloaded from the CCDC.
;
_audit_creation_date             2023-04-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
yamakou@shujitsu.ac.jp
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H26 B F2 N3'
_chemical_formula_sum            'C24 H26 B F2 N3'
_chemical_formula_weight         405.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H26 B F2 N3'
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'
N N 0.0061 0.0033 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.7244(8)
_cell_length_b                   10.0495(3)
_cell_length_c                   12.6371(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.399(5)
_cell_angle_gamma                90
_cell_volume                     2109.78(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14366
_cell_measurement_temperature    130
_cell_measurement_theta_max      29.7460
_cell_measurement_theta_min      2.4430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35577
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.853
_diffrn_reflns_theta_min         2.658
_diffrn_ambient_temperature      130
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00  77.00   0.25    5.00    --  -13.00  55.00-108.00  720
  2  ω    -83.00  53.00   0.25    5.00    --  -13.00  55.00-180.00  544
  3  ω    -39.00  21.00   0.25    5.00    --  -13.00  27.00 108.00  240
  4  ω     14.00  75.00   0.25    5.00    --  -13.00  55.00 108.00  244
  5  ω     -1.00  59.25   0.25    5.00    --  -13.00  55.00  36.00  241
  6  ω   -103.00  76.50   0.25    5.00    --  -13.00  55.00 -36.00  718
;
_diffrn_measurement_device       'AFC11 (Right): Eulerian 3 circle'
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0088945000
_diffrn_orient_matrix_UB_12      0.0544887000
_diffrn_orient_matrix_UB_13      0.0380586000
_diffrn_orient_matrix_UB_21      0.0367851000
_diffrn_orient_matrix_UB_22      -0.0307679000
_diffrn_orient_matrix_UB_23      0.0326841000
_diffrn_orient_matrix_UB_31      0.0198029000
_diffrn_orient_matrix_UB_32      0.0326669000
_diffrn_orient_matrix_UB_33      -0.0326827000
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4251
_reflns_number_total             5666
_reflns_odcompleteness_completeness 93.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.79
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         5666
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0482
_refine_ls_restrained_S_all      1.041
_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)+(0.0636P)²+0.5952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1282
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=1-FVAR(1)
 Sof(C00S)=Sof(H00R)=Sof(H00S)=Sof(H00T)=FVAR(1)
 Sof(C00V)=Sof(H00Z)=Sof(HA)=Sof(HB)=1-FVAR(2)
 Sof(C00U)=Sof(H00X)=Sof(H00Y)=Sof(H)=FVAR(2)
 Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=1-FVAR(3)
 Sof(C00T)=Sof(H00U)=Sof(H00V)=Sof(H00W)=FVAR(3)
3.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00F(H00F), C00H(H00H), C00I(H00I), C00K(H00K),
 C00L(H00L), C00M(H00M)
3.b Idealised Me refined as rotating group:
 C00N(H00C,H00D,H00E), C00P(H00G,H00J,H00N), C00Q(H00O,H00P,H00Q), C00S(H00R,
 H00S,H00T), C00T(H00U,H00V,H00W), C00U(H00X,H00Y,H), C1(H1A,H1B,H1C),
 C00V(H00Z,HA,HB), C2(H2A,H2B,H2C)
;
_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 0.52469(5) 0.79842(10) 0.38579(8) 0.0435(3) Uani 1 1 d . . . . .
F002 F 0.59962(6) 0.91643(8) 0.53781(10) 0.0503(3) Uani 1 1 d . . . . .
N003 N 0.54127(6) 0.70824(10) 0.56816(9) 0.0213(2) Uani 1 1 d . . . . .
N004 N 0.65608(6) 0.71398(10) 0.49453(9) 0.0213(2) Uani 1 1 d . . . . .
N005 N 0.42927(7) 0.71791(12) 0.63059(10) 0.0301(3) Uani 1 1 d . . . . .
C006 C 0.73188(7) 0.34170(12) 0.63425(10) 0.0190(2) Uani 1 1 d . . . . .
C007 C 0.63303(7) 0.52207(12) 0.60182(10) 0.0185(2) Uani 1 1 d . . . . .
C008 C 0.56256(7) 0.58406(12) 0.61327(10) 0.0197(3) Uani 1 1 d . . . . .
C009 C 0.67503(7) 0.59138(12) 0.54426(10) 0.0189(2) Uani 1 1 d . . . . .
C00A C 0.66305(7) 0.39673(12) 0.64659(10) 0.0193(2) Uani 1 1 d . . . . .
H00A H 0.635613 0.347939 0.686518 0.023 Uiso 1 1 calc R U . . .
C00B C 0.77243(8) 0.41443(12) 0.57531(10) 0.0200(3) Uani 1 1 d . . . . .
H00B H 0.819278 0.378183 0.566156 0.024 Uiso 1 1 calc R U . . .
C00C C 0.74471(7) 0.53858(12) 0.53040(10) 0.0195(3) Uani 1 1 d . . . . .
C00D C 0.76492(8) 0.20501(12) 0.68209(11) 0.0216(3) Uani 1 1 d . . . . .
C00E C 0.77139(8) 0.63838(12) 0.46851(10) 0.0203(3) Uani 1 1 d . . . . .
C00F C 0.51405(8) 0.52464(13) 0.66653(11) 0.0232(3) Uani 1 1 d . . . . .
H00F H 0.526052 0.438083 0.698165 0.028 Uiso 1 1 calc R U . . .
C00G C 0.71503(8) 0.74363(12) 0.44710(10) 0.0208(3) Uani 1 1 d . . . . .
C00H C 0.72411(8) 0.85586(13) 0.38781(11) 0.0247(3) Uani 1 1 d . . . . .
H00H H 0.685676 0.925832 0.370533 0.030 Uiso 1 1 calc R U . . .
C00I C 0.83782(8) 0.64793(12) 0.43450(11) 0.0222(3) Uani 1 1 d . . . . .
H00I H 0.875363 0.576752 0.449413 0.027 Uiso 1 1 calc R U . . .
C00J C 0.84969(8) 0.76129(13) 0.37866(11) 0.0230(3) Uani 1 1 d . . . . .
C00K C 0.79076(8) 0.86242(13) 0.35481(11) 0.0256(3) Uani 1 1 d . . . . .
H00K H 0.797161 0.938562 0.314193 0.031 Uiso 1 1 calc R U . . .
C00L C 0.44866(9) 0.59367(14) 0.67234(11) 0.0278(3) Uani 1 1 d . . . . .
H00L H 0.415398 0.552001 0.707474 0.033 Uiso 1 1 calc R U . . .
C00M C 0.47606(8) 0.76839(14) 0.58030(11) 0.0267(3) Uani 1 1 d . . . . .
H00M H 0.463214 0.855161 0.549429 0.032 Uiso 1 1 calc R U . . .
C00N C 0.71013(9) 0.13384(13) 0.73420(13) 0.0288(3) Uani 1 1 d . . . . .
H00C H 0.706889 0.185919 0.798042 0.043 Uiso 1 1 calc R U . . .
H00D H 0.732154 0.045556 0.760648 0.043 Uiso 1 1 calc R U . . .
H00E H 0.656193 0.124410 0.677326 0.043 Uiso 1 1 calc R U . . .
C00O C 0.92428(8) 0.77302(13) 0.34412(12) 0.0258(3) Uani 1 1 d . . . . .
C00P C 0.84812(9) 0.22282(14) 0.77377(13) 0.0307(3) Uani 1 1 d . . . . .
H00G H 0.884402 0.266462 0.741172 0.046 Uiso 1 1 calc R U . . .
H00J H 0.869984 0.135528 0.803666 0.046 Uiso 1 1 calc R U . . .
H00N H 0.843057 0.277827 0.834983 0.046 Uiso 1 1 calc R U . . .
C00Q C 0.77160(9) 0.11749(13) 0.58573(12) 0.0291(3) Uani 1 1 d . . . . .
H00O H 0.718997 0.112390 0.525141 0.044 Uiso 1 1 calc R U . . .
H00P H 0.789079 0.027882 0.614472 0.044 Uiso 1 1 calc R U . . .
H00Q H 0.810960 0.156488 0.556248 0.044 Uiso 1 1 calc R U . . .
B00R B 0.58288(9) 0.79081(14) 0.49298(14) 0.0263(3) Uani 1 1 d . . . . .
C00S C 0.99852(14) 0.7349(5) 0.4417(3) 0.0383(9) Uani 0.730(11) 1 d . . P A 1
H00R H 1.002712 0.790574 0.507164 0.057 Uiso 0.730(11) 1 calc R U P A 1
H00S H 1.046223 0.748124 0.420614 0.057 Uiso 0.730(11) 1 calc R U P A 1
H00T H 0.994956 0.641146 0.460800 0.057 Uiso 0.730(11) 1 calc R U P A 1
C00T C 0.93665(15) 0.9165(2) 0.3088(3) 0.0396(8) Uani 0.770(7) 1 d . . P A 1
H00U H 0.891001 0.941736 0.241608 0.059 Uiso 0.770(7) 1 calc R U P A 1
H00V H 0.986461 0.920816 0.291720 0.059 Uiso 0.770(7) 1 calc R U P A 1
H00W H 0.940321 0.977956 0.370618 0.059 Uiso 0.770(7) 1 calc R U P A 1
C00U C 0.91201(19) 0.6837(4) 0.2406(3) 0.0423(9) Uani 0.786(11) 1 d . . P A 1
H00X H 0.904871 0.591273 0.259958 0.063 Uiso 0.786(11) 1 calc R U P A 1
H00Y H 0.959256 0.689999 0.217541 0.063 Uiso 0.786(11) 1 calc R U P A 1
H H 0.864098 0.712970 0.178397 0.063 Uiso 0.786(11) 1 calc R U P A 1
C1 C 0.9909(5) 0.6594(17) 0.4028(12) 0.054(4) Uani 0.270(11) 1 d . . P A 2
H1A H 1.003933 0.661593 0.484782 0.081 Uiso 0.270(11) 1 calc R U P A 2
H1B H 1.039707 0.676393 0.385280 0.081 Uiso 0.270(11) 1 calc R U P A 2
H1C H 0.969213 0.571759 0.373733 0.081 Uiso 0.270(11) 1 calc R U P A 2
C00V C 0.9056(5) 0.766(2) 0.2236(7) 0.052(5) Uani 0.214(11) 1 d . . P A 2
H00Z H 0.876688 0.682754 0.194764 0.078 Uiso 0.214(11) 1 calc R U P A 2
HA H 0.955688 0.767636 0.207022 0.078 Uiso 0.214(11) 1 calc R U P A 2
HB H 0.871926 0.841668 0.187188 0.078 Uiso 0.214(11) 1 calc R U P A 2
C2 C 0.9706(7) 0.8998(10) 0.3967(14) 0.066(5) Uani 0.230(7) 1 d . . P A 2
H2A H 0.933573 0.975693 0.379604 0.098 Uiso 0.230(7) 1 calc R U P A 2
H2B H 1.013204 0.915974 0.365401 0.098 Uiso 0.230(7) 1 calc R U P A 2
H2C H 0.994716 0.888748 0.478746 0.098 Uiso 0.230(7) 1 calc R U P A 2


_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 B00R 1.3894(18) . ?
F002 B00R 1.3732(17) . ?
N003 C008 1.3693(16) . ?
N003 C00M 1.3597(16) . ?
N003 B00R 1.6196(19) . ?
N004 C009 1.3707(15) . ?
N004 C00G 1.4058(17) . ?
N004 B00R 1.5041(18) . ?
N005 C00L 1.3523(18) . ?
N005 C00M 1.3100(19) . ?
C006 C00A 1.3968(17) . ?
C006 C00B 1.4066(17) . ?
C006 C00D 1.5325(16) . ?
C007 C008 1.4474(17) . ?
C007 C009 1.3949(17) . ?
C007 C00A 1.4072(17) . ?
C008 C00F 1.3972(18) . ?
C009 C00C 1.4101(17) . ?
C00A H00A 0.9500 . ?
C00B H00B 0.9500 . ?
C00B C00C 1.3877(17) . ?
C00C C00E 1.4487(17) . ?
C00D C00N 1.5278(18) . ?
C00D C00P 1.5355(19) . ?
C00D C00Q 1.5397(18) . ?
C00E C00G 1.4148(17) . ?
C00E C00I 1.3903(18) . ?
C00F H00F 0.9500 . ?
C00F C00L 1.3746(18) . ?
C00G C00H 1.3941(17) . ?
C00H H00H 0.9500 . ?
C00H C00K 1.385(2) . ?
C00I H00I 0.9500 . ?
C00I C00J 1.3941(17) . ?
C00J C00K 1.4125(19) . ?
C00J C00O 1.5344(19) . ?
C00K H00K 0.9500 . ?
C00L H00L 0.9500 . ?
C00M H00M 0.9500 . ?
C00N H00C 0.9800 . ?
C00N H00D 0.9800 . ?
C00N H00E 0.9800 . ?
C00O C00S 1.506(3) . ?
C00O C00T 1.548(2) . ?
C00O C00U 1.538(3) . ?
C00O C1 1.624(9) . ?
C00O C00V 1.443(9) . ?
C00O C2 1.536(9) . ?
C00P H00G 0.9800 . ?
C00P H00J 0.9800 . ?
C00P H00N 0.9800 . ?
C00Q H00O 0.9800 . ?
C00Q H00P 0.9800 . ?
C00Q H00Q 0.9800 . ?
C00S H00R 0.9800 . ?
C00S H00S 0.9800 . ?
C00S H00T 0.9800 . ?
C00T H00U 0.9800 . ?
C00T H00V 0.9800 . ?
C00T H00W 0.9800 . ?
C00U H00X 0.9800 . ?
C00U H00Y 0.9800 . ?
C00U H 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C00V H00Z 0.9800 . ?
C00V HA 0.9800 . ?
C00V HB 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C008 N003 B00R 126.54(10) . . ?
C00M N003 C008 118.68(11) . . ?
C00M N003 B00R 114.66(11) . . ?
C009 N004 C00G 106.63(10) . . ?
C009 N004 B00R 122.67(11) . . ?
C00G N004 B00R 130.66(11) . . ?
C00M N005 C00L 115.41(12) . . ?
C00A C006 C00B 118.74(11) . . ?
C00A C006 C00D 122.64(11) . . ?
C00B C006 C00D 118.63(11) . . ?
C009 C007 C008 118.24(11) . . ?
C009 C007 C00A 117.45(11) . . ?
C00A C007 C008 124.30(11) . . ?
N003 C008 C007 118.22(11) . . ?
N003 C008 C00F 117.61(11) . . ?
C00F C008 C007 124.17(11) . . ?
N004 C009 C007 126.72(11) . . ?
N004 C009 C00C 111.50(11) . . ?
C007 C009 C00C 121.78(11) . . ?
C006 C00A C007 122.14(11) . . ?
C006 C00A H00A 118.9 . . ?
C007 C00A H00A 118.9 . . ?
C006 C00B H00B 119.7 . . ?
C00C C00B C006 120.68(11) . . ?
C00C C00B H00B 119.7 . . ?
C009 C00C C00E 105.75(10) . . ?
C00B C00C C009 119.21(11) . . ?
C00B C00C C00E 135.03(12) . . ?
C006 C00D C00P 109.12(10) . . ?
C006 C00D C00Q 108.92(10) . . ?
C00N C00D C006 112.13(11) . . ?
C00N C00D C00P 108.47(11) . . ?
C00N C00D C00Q 108.00(11) . . ?
C00P C00D C00Q 110.18(11) . . ?
C00G C00E C00C 106.21(11) . . ?
C00I C00E C00C 133.28(11) . . ?
C00I C00E C00G 120.46(11) . . ?
C008 C00F H00F 120.6 . . ?
C00L C00F C008 118.82(12) . . ?
C00L C00F H00F 120.6 . . ?
N004 C00G C00E 109.89(11) . . ?
C00H C00G N004 130.01(12) . . ?
C00H C00G C00E 120.10(12) . . ?
C00G C00H H00H 121.0 . . ?
C00K C00H C00G 118.09(12) . . ?
C00K C00H H00H 121.0 . . ?
C00E C00I H00I 119.8 . . ?
C00E C00I C00J 120.42(12) . . ?
C00J C00I H00I 119.8 . . ?
C00I C00J C00K 117.72(12) . . ?
C00I C00J C00O 120.25(12) . . ?
C00K C00J C00O 122.03(11) . . ?
C00H C00K C00J 123.13(12) . . ?
C00H C00K H00K 118.4 . . ?
C00J C00K H00K 118.4 . . ?
N005 C00L C00F 123.32(13) . . ?
N005 C00L H00L 118.3 . . ?
C00F C00L H00L 118.3 . . ?
N003 C00M H00M 116.9 . . ?
N005 C00M N003 126.11(13) . . ?
N005 C00M H00M 116.9 . . ?
C00D C00N H00C 109.5 . . ?
C00D C00N H00D 109.5 . . ?
C00D C00N H00E 109.5 . . ?
H00C C00N H00D 109.5 . . ?
H00C C00N H00E 109.5 . . ?
H00D C00N H00E 109.5 . . ?
C00J C00O C00T 112.11(13) . . ?
C00J C00O C00U 108.47(13) . . ?
C00J C00O C1 112.2(3) . . ?
C00J C00O C2 108.9(4) . . ?
C00S C00O C00J 109.95(14) . . ?
C00S C00O C00T 107.6(2) . . ?
C00S C00O C00U 111.8(3) . . ?
C00U C00O C00T 106.9(2) . . ?
C00V C00O C00J 113.2(4) . . ?
C00V C00O C1 108.0(10) . . ?
C00V C00O C2 113.0(11) . . ?
C2 C00O C1 101.0(9) . . ?
C00D C00P H00G 109.5 . . ?
C00D C00P H00J 109.5 . . ?
C00D C00P H00N 109.5 . . ?
H00G C00P H00J 109.5 . . ?
H00G C00P H00N 109.5 . . ?
H00J C00P H00N 109.5 . . ?
C00D C00Q H00O 109.5 . . ?
C00D C00Q H00P 109.5 . . ?
C00D C00Q H00Q 109.5 . . ?
H00O C00Q H00P 109.5 . . ?
H00O C00Q H00Q 109.5 . . ?
H00P C00Q H00Q 109.5 . . ?
F001 B00R N003 105.37(11) . . ?
F001 B00R N004 112.62(12) . . ?
F002 B00R F001 109.38(12) . . ?
F002 B00R N003 107.83(12) . . ?
F002 B00R N004 113.90(12) . . ?
N004 B00R N003 107.24(10) . . ?
C00O C00S H00R 109.5 . . ?
C00O C00S H00S 109.5 . . ?
C00O C00S H00T 109.5 . . ?
H00R C00S H00S 109.5 . . ?
H00R C00S H00T 109.5 . . ?
H00S C00S H00T 109.5 . . ?
C00O C00T H00U 109.5 . . ?
C00O C00T H00V 109.5 . . ?
C00O C00T H00W 109.5 . . ?
H00U C00T H00V 109.5 . . ?
H00U C00T H00W 109.5 . . ?
H00V C00T H00W 109.5 . . ?
C00O C00U H00X 109.5 . . ?
C00O C00U H00Y 109.5 . . ?
C00O C00U H 109.5 . . ?
H00X C00U H00Y 109.5 . . ?
H00X C00U H 109.5 . . ?
H00Y C00U H 109.5 . . ?
C00O C1 H1A 109.5 . . ?
C00O C1 H1B 109.5 . . ?
C00O C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C00O C00V H00Z 109.5 . . ?
C00O C00V HA 109.5 . . ?
C00O C00V HB 109.5 . . ?
H00Z C00V HA 109.5 . . ?
H00Z C00V HB 109.5 . . ?
HA C00V HB 109.5 . . ?
C00O C2 H2A 109.5 . . ?
C00O C2 H2B 109.5 . . ?
C00O C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?

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
N003 C008 C00F C00L -0.86(18) . . . . ?
N004 C009 C00C C00B -179.77(11) . . . . ?
N004 C009 C00C C00E 1.00(14) . . . . ?
N004 C00G C00H C00K 176.82(13) . . . . ?
C006 C00B C00C C009 -0.12(18) . . . . ?
C006 C00B C00C C00E 178.83(13) . . . . ?
C007 C008 C00F C00L 179.87(12) . . . . ?
C007 C009 C00C C00B -0.11(18) . . . . ?
C007 C009 C00C C00E -179.34(11) . . . . ?
C008 N003 C00M N005 -1.1(2) . . . . ?
C008 N003 B00R F001 112.90(13) . . . . ?
C008 N003 B00R F002 -130.36(12) . . . . ?
C008 N003 B00R N004 -7.30(17) . . . . ?
C008 C007 C009 N004 -1.04(18) . . . . ?
C008 C007 C009 C00C 179.36(11) . . . . ?
C008 C007 C00A C006 -179.32(11) . . . . ?
C008 C00F C00L N005 -1.1(2) . . . . ?
C009 N004 C00G C00E -0.40(13) . . . . ?
C009 N004 C00G C00H -179.54(13) . . . . ?
C009 N004 B00R F001 -110.24(14) . . . . ?
C009 N004 B00R F002 124.45(14) . . . . ?
C009 N004 B00R N003 5.23(16) . . . . ?
C009 C007 C008 N003 -0.75(16) . . . . ?
C009 C007 C008 C00F 178.52(11) . . . . ?
C009 C007 C00A C006 -0.37(17) . . . . ?
C009 C00C C00E C00G -1.19(13) . . . . ?
C009 C00C C00E C00I 176.22(13) . . . . ?
C00A C006 C00B C00C 0.10(18) . . . . ?
C00A C006 C00D C00N 4.96(17) . . . . ?
C00A C006 C00D C00P -115.25(13) . . . . ?
C00A C006 C00D C00Q 124.43(13) . . . . ?
C00A C007 C008 N003 178.20(11) . . . . ?
C00A C007 C008 C00F -2.54(19) . . . . ?
C00A C007 C009 N004 179.95(11) . . . . ?
C00A C007 C009 C00C 0.34(17) . . . . ?
C00B C006 C00A C007 0.15(18) . . . . ?
C00B C006 C00D C00N -174.87(11) . . . . ?
C00B C006 C00D C00P 64.92(14) . . . . ?
C00B C006 C00D C00Q -55.40(15) . . . . ?
C00B C00C C00E C00G 179.76(14) . . . . ?
C00B C00C C00E C00I -2.8(2) . . . . ?
C00C C00E C00G N004 1.00(14) . . . . ?
C00C C00E C00G C00H -179.76(11) . . . . ?
C00C C00E C00I C00J -177.22(13) . . . . ?
C00D C006 C00A C007 -179.68(11) . . . . ?
C00D C006 C00B C00C 179.94(11) . . . . ?
C00E C00G C00H C00K -2.25(18) . . . . ?
C00E C00I C00J C00K -2.22(18) . . . . ?
C00E C00I C00J C00O 178.35(12) . . . . ?
C00G N004 C009 C007 179.97(12) . . . . ?
C00G N004 C009 C00C -0.39(14) . . . . ?
C00G N004 B00R F001 67.44(17) . . . . ?
C00G N004 B00R F002 -57.87(19) . . . . ?
C00G N004 B00R N003 -177.09(11) . . . . ?
C00G C00E C00I C00J -0.11(18) . . . . ?
C00G C00H C00K C00J -0.2(2) . . . . ?
C00I C00E C00G N004 -176.81(11) . . . . ?
C00I C00E C00G C00H 2.43(18) . . . . ?
C00I C00J C00K C00H 2.4(2) . . . . ?
C00I C00J C00O C00S -47.2(3) . . . . ?
C00I C00J C00O C00T -166.87(17) . . . . ?
C00I C00J C00O C00U 75.3(2) . . . . ?
C00I C00J C00O C1 -12.2(8) . . . . ?
C00I C00J C00O C00V 110.2(10) . . . . ?
C00I C00J C00O C2 -123.2(7) . . . . ?
C00K C00J C00O C00S 133.4(2) . . . . ?
C00K C00J C00O C00T 13.7(2) . . . . ?
C00K C00J C00O C00U -104.1(2) . . . . ?
C00K C00J C00O C1 168.4(8) . . . . ?
C00K C00J C00O C00V -69.2(10) . . . . ?
C00K C00J C00O C2 57.4(7) . . . . ?
C00L N005 C00M N003 -0.8(2) . . . . ?
C00M N003 C008 C007 -178.78(11) . . . . ?
C00M N003 C008 C00F 1.91(17) . . . . ?
C00M N003 B00R F001 -63.11(14) . . . . ?
C00M N003 B00R F002 53.63(15) . . . . ?
C00M N003 B00R N004 176.68(11) . . . . ?
C00M N005 C00L C00F 1.9(2) . . . . ?
C00O C00J C00K C00H -178.16(12) . . . . ?
B00R N003 C008 C007 5.35(18) . . . . ?
B00R N003 C008 C00F -173.96(11) . . . . ?
B00R N003 C00M N005 175.21(13) . . . . ?
B00R N004 C009 C007 -1.86(19) . . . . ?
B00R N004 C009 C00C 177.77(11) . . . . ?
B00R N004 C00G C00E -178.37(12) . . . . ?
B00R N004 C00G C00H 2.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.910
_oxdiff_exptl_absorpt_empirical_full_min 0.610
